[ CAS No. 3420-02-8 ] {[proInfo.proName]}

Name: 3420-02-8|6-Methyl-1H-indole|98%
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Quality Control of [ 3420-02-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 3420-02-8 ]

CAS No. :	3420-02-8	MDL No. :	MFCD00005682
Formula :	C₉H₉N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ONYNOPPOVKYGRS-UHFFFAOYSA-N
M.W :	131.17	Pubchem ID :	137928
Synonyms :	6-Methylindole

Calculated chemistry of [ 3420-02-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.26
TPSA :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	3.32
Log Po/w (WLOGP) :	2.48
Log Po/w (MLOGP) :	1.89
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	2.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.0509 mg/ml ; 0.000388 mol/l
Class :	Soluble
Log S (Ali) :	-3.33
Solubility :	0.0616 mg/ml ; 0.00047 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.63
Solubility :	0.0305 mg/ml ; 0.000232 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 3420-02-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3420-02-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3420-02-8 ]
Downstream synthetic route of [ 3420-02-8 ]

[ 3420-02-8 ] Synthesis Path-Upstream 1~6

1
[ 3420-02-8 ]
[ 5649-36-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9480 - 9497

2
[ 3420-02-8 ]
[ 209920-43-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2734 - 2737
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 17, p. 7293 - 7316
[3] Patent: WO2009/125923, 2009, A2,

3
[ 3420-02-8 ]
[ 68-12-2 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: at 0 - 20℃; for 1.5 h; Stage #2: for 1.5 h; Heating / reflux	Example 4; 1. Synthesis of indole derivatives; 1) Synthesis of 3-cyanoindole derivatives; [Show Image] Nine objective compounds were prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-6-ether in dimethyl sulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order (the following Table 2). In addition, XO-CH172 and XO-CH183 (R is a 2-methyl group or a 5-methoxy group, respectively) were prepared from the step (2) using the corresponding aldehydes purchased.; 1) Synthesis of XO-CH200; XO-CH180 Under an argon atmosphere, 6-methylindole (1.004 g, 7. 62 mmol) was dissolved in dimethylformamide (10 mL), and to the solution was added phosphorus oxychloride (2 mL) under ice-cooling. The mixture was stirred for 1.5 hours at room temperature. To the reaction mixture was added dropwise an aqueous sodium hydroxide solution (5g/15mL) under ice-cooling. The mixture was heated for reflux for 1.5 hours. To the reaction mixture was added water under ice-cooling, and the mixture was adjusted to pH3 with concentrated hydrochloric acid. The solid was collected by filtration and dried at 60°C under reduced pressure to give XO-CH180 as a pale brown solid (1.14 g, 94percent yield).
79%	Stage #1: at 0℃; Stage #2: at 35℃; for 1 h;	General procedure: The Vilsmeier-Haack reagent was prepared by adding POCl₃ (60 mmol, 6 mL) dropwise to ice-cold dry DMF (30 mL) whilst stirring. The mixture was then stirred for 10-15 min at 0 °C. Compound 3b or 3e (10 mmol) was added as a solution in DMF (5 mL) to the above Vilsmeier-Haack reagent. The stirred mixture was then heated at 35 °C for 1 h. After cooling, ice water (6 mL) and a 30percent aqueous solution of NaOH (13 mL) were added successively, and the mixture was heated at reflux for 20 min and allowed to cool. The mixture was extracted with CH₂Cl₂ (20 mL*3). The extracts were dried over Na₂SO₄, evaporated under reduced pressure to remove the solvent, and the crude product was purified by flash column chromatography using 15-25percent acetone/petroleum ether (60-90 °C) as eluent to give the corresponding intermediate compound 4b or 4e, respectively.

Reference： [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705
[2] Patent: EP1932833, 2008, A1, . Location in patent: Page/Page column 15; 19
[3] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[4] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 776 - 783
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1301 - 1305
[6] Patent: US5563147, 1996, A,
[7] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3780 - 3790
[8] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7274 - 7277
[9] Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254[10] Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5
[11] Organic Letters, 2015, vol. 17, # 12, p. 3186 - 3189
[12] Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107
[13] Organic Letters, 2017, vol. 19, # 10, p. 2502 - 2505
[14] Chemical Communications, 2017, vol. 53, # 43, p. 5834 - 5837

4
[ 3420-02-8 ]
[ 100-97-0 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iodine; oxygen; pyrographite In N,N-dimethyl-formamide at 120℃; for 0.8 h;	General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I₂(0.2 mmol, 0.0507g, 20 molpercent) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 ^oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO₃ solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na₂SO₄and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 30, p. 2877 - 2880

5
[ 3420-02-8 ]
[ 50-00-0 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With iron(III) chloride; ammonia In water; N,N-dimethyl-formamide at 130℃; for 1 h;	General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37percent aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25percent aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 molpercent), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane–EtOAc).

Reference： [1] Synlett, 2017, vol. 28, # 19, p. 2670 - 2674

6
[ 3420-02-8 ]
[ 1196-70-9 ]

Reference： [1] Tetrahedron Letters, 1989, vol. 30, # 45, p. 6117 - 6120

[ 3420-02-8 ] Synthesis Path-Downstream 1~88

1
[ 209920-43-4 ]
[ 3420-02-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1955,vol. 593,p. 91,109

2
[ 3420-02-8 ]
[ 592-33-6 ]
[ 112291-05-1 ]

Reference： [1]Heterocycles,1987,vol. 26,p. 1207 - 1210

3
[ 3420-02-8 ]
[ 98-09-9 ]
[ 116325-11-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;	The synthetic route of the N-benzenesulfonyl-6-methylindole compound is as follows: Weighed6-methylindole (lmmol),Substituted benzenesulfonyl chloride (1.2 mmol)Sodium hydroxide (1.8 mmol) and TEBA (0. Lmmol) in a 50 mL flask,Dichloromethane (5 mL) was added,Room temperature reaction 1 ~ 2h,TLC trace detection to complete reaction,Add water (10 mL) to terminate the reaction.Extracted with dichloromethane (20 mL x 3 times)Combine organic phase,The organic phase was washed with saturated sodium chloride solution (10 mL)Dried over anhydrous sodium sulfate,Concentrated under reduced pressure,Thin layer chromatography separates the required pure product
95.1%	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	8.5. General procedure for the synthesis of 2-aryl-1-(phenylsulfonyl)-1H-imidazole (6a-b, 19), 1-(phenylsulfonyl)-1H-indole (10a-f, 10h), and 1-(phenylsulfonyl)-1H-benzo[d]imidazole (10g) General procedure: To a solution of imidazoles (5a, 5b, 18), indoles (9a-f, 9h), or benzimidazole (9g) (1.3-3.5 g, 10 mmol) in anhydrous THF (200 ml) at 0 °C was added sodium hydride (60% dispersion in mineral oil, 48 mg, 12 mmol) and stirred for 20 min. 4-Methoxy-benzenesulfonyl chloride (2.5 g, 12 mmol) (for 6b) or benzenesulfonyl chloride (2.1 g, 12 mmol) (for others) was added, and the reaction mixture was stirred overnight. After dilution by 200 ml of saturated NaHCO3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (600 ml). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane/ethyl acetate, 2:1) to give a pale solid. Yield: 40-95%.
88%	With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In benzene for 0.5h; Ambient temperature;

75%	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 0.5h;
71%	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran for 1h;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 0℃; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃;
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃;	C.C.10.1 Step-1 : Synthesis of 1 -(benzenesulfonyl)-6-methyl-indole XII-10a To a solution of 6-methyl-1H-indole (1 g, 7.39 mmol) in THF (20 mL), sodium hydride (60 % in paraffin, 0.35 g, 8.9 mmol) was added at 0 °C. The solution was stirred for 30 min being allowed to warm up from 0 °C to rt. Subsequently, benzenesulfonic acid chloride (1 .1 mL, 8.9 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight and hydrolyzed with water. It was then extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSCL and concentrated under vacuum. The residue was purified by column chromatography (eluent: 25-40% AcOEt in heptane) yielding 1 .97 g of 1 -(benzenesulfonyl)-6-methyl-indole XII-10a as a colourless oil. (1148) Yield: 70% (1149) Basic LCMS Method 1 (ES ): 270 (M-H)-, 71 % purity

Reference： [1]Current Patent Assignee: HENAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105052936, 2017, B Location in patent: Paragraph 0064-0069
[2]Location in patent: experimental part Chen, Jianjun; Li, Chien-Ming; Wang, Jin; Ahn, Sunjoo; Wang, Zhao; Lu, Yan; Dalton, James T.; Miller, Duane D.; Li, Wei [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 4782 - 4795]
[3]Wenkert,E.; Moeller,P.D.; Piettre,S.R. [Journal of the American Chemical Society, 1988, vol. 110, p. 7188]
[4]Chen, Siwei; Cai, Min; Huang, Junru; Yao, Hequan; Lin, Aijun [Organic Letters, 2021, vol. 23, # 6, p. 2212 - 2216]
[5]Mahboobi, Siavosh; Uecker, Andrea; Sellmer, Andreas; Cénac, Christophe; Höcher, Heymo; Pongratz, Herwig; Eichhorn, Emerich; Hufsky, Harald; Trümpler, Antje; Sicker, Marit; Heidel, Florian; Fischer, Thomas; Stocking, Carol; Elz, Sigurd; Böhmer, Frank-D.; Dove, Stefan [Journal of Medicinal Chemistry, 2006, vol. 49, # 11, p. 3101 - 3115]
[6]Ran, Jun-Qiang; Huang, Ning; Xu, Hui; Yang, Liu-Meng; Lv, Min; Zheng, Yong-Tang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3534 - 3536]
[7]Che, Zhiping; Zhang, Shaoyong; Shao, Yonghua; Fan, Lingling; Xu, Hui; Yu, Xiang; Zhi, Xiaoyan; Yao, Xiaojun; Zhang, Rui [Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705]
[8]Zhou, Han-Jie; Wang, Jinhai; Yao, Bing; Wong, Steve; Djakovic, Stevan; Kumar, Brajesh; Rice, Julie; Valle, Eduardo; Soriano, Ferdie; Menon, Mary-Kamala; Madriaga, Antonett; Kiss Von Soly, Szerenke; Kumar, Abhinav; Parlati, Francesco; Yakes, F. Michael; Shawver, Laura; Le Moigne, Ronan; Anderson, Daniel J.; Rolfe, Mark; Wustrow, David [Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9480 - 9497]
[9]Current Patent Assignee: UNIVERSITY OF BONN; UCB; UCB PHARMA GMBH - WO2019/243303, 2019, A1 Location in patent: Page/Page column 92; 102

4
[ 3420-02-8 ]
[ 74-88-4 ]
[ 5621-15-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydride In tetrahydrofuran for 4h;
76%	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;
	With sodium hydride

	Stage #1: 6-methylindole With potassium hydroxide In N,N-dimethyl-formamide Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃;
	With potassium <i>tert</i>-butylate In diethyl ether at 0℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	General procedure B: (Substrate 1b-d, 1g-1i) General procedure: To a solution of indole (12.0 mmol) in DMF (60 mL) at 0° C was added NaH (60% dispersion in mineral oil, 14.4 mmol) slowly. The mixture was stirred at this temperature for 30 minutes, then methyl iodide (13.2 mmol) was added drop-wise via syringe. Then the reaction was gradually warmed up to room temperature and stirred for 3 hours. The reaction was quenched with saturated aqueous NH4Cl and diluted with EtOAc (60 mL) and water (60 mL), the organic layer was separated and the aqueous layer was extracted with EtOAc (2×60 mL). The combined organic layers were washed with water (4×60 mL) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to furnish the desired N-methyl indole as colorless oil that required no further purification.
	Stage #1: 6-methylindole; methyl iodide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil Inert atmosphere;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃;
	With potassium hydroxide In dimethyl sulfoxide
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran for 0.5h; Darkness; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 12h;	5.1.2 Synthesis of N-methylindole analogues 2a-i General procedure: To a solution of indoles 1a-i (10mmol) in dry tetrahydrofuran (THF; 25mL), NaH (30mmol) was added. After the mixture was stirred 30min, CH3I (30mmol) in 5mL THF was added dropwise under 0°C. The reaction mixture was stirred at room temperature for 12h in the dark. Then the reaction mixture was cooled to room temperature,diluted with 30mL saturated NH4Cl solution, and extracted with EtOAc (3×30mL). The organic layer dried over anhydrous MgSO4 and concentrated in vacuo. The pure products 2a-i was obtained by column chromatography on silica gel (Petroleum ether/EtOAc=20:1) with yield of 90%-99%.
	With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h;	4.2. Preparation of N-methyl-1H-indoles General procedure: To a solution of indole (1.17 g, 10 mmol) and potassium hydroxide (2.8 g, 50 mmol) in anhydrous DMF (20 ml) was added iodomethane (2.13 g, 15 mmol). The reaction mixture was stirred at room temperature for 2 h. Then H2O was added to the mixture. The water layer was extracted with EtOAc (50 ml * 3). The organic layer was combined and dried over Na2SO4. After filtration and evaporation, the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate 8/1) to afford N-methyl-1H-indole (1.24 g, 94%).
	With sodium hydride In N,N-dimethyl-formamide
	With potassium hydroxide In dimethyl sulfoxide at 20℃;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 25℃;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Cooling; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h; Cooling; Inert atmosphere;
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃;
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.25h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.16667h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;

Reference： [1]Hao, Tonggang; Huang, Long; Wei, Yin; Shi, Min [Organic Letters, 2021, vol. 23, # 13, p. 5133 - 5137]
[2]Lane, Benjamin S.; Brown, Meghann A.; Sames, Dalibor [Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057]
[3]Nakatsuka, Shin-ichi; Ueda, Kazuo; Asano, Osamu; Goto, Toshio [Heterocycles, 1987, vol. 26, # 1, p. 65 - 68]
[4]Zhang, Hua; Liu, Dong; Chen, Caiyou; Liu, Chao; Lei, Aiwen [Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9581 - 9585]
[5]Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei [Chemical Communications, 2012, vol. 48, # 89, p. 11023 - 11025] Xing, Qi; Li, Pan; Lv, Hui; Lang, Rui; Xia, Chungu; Li, Fuwei [Chemical Communications, 2014, vol. 50, # 81, p. 12181 - 12184]
[6]Zeng, Fanlong; Alper, Howard [Organic Letters, 2013, vol. 15, # 8, p. 2034 - 2037] Pu, Xingwen; Zhang, Mangang; Lan, Jingbo; Chen, Shuyou; Liu, Zheng; Liang, Wenbo; Yang, Yudong; Zhang, Min; You, Jingsong [Organic Letters, 2019, vol. 21, # 4, p. 1139 - 1143]
[7]Wang, Huifei; Liu, Dong; Chen, Huiyu; Li, Jing; Wang, David Zhigang [Tetrahedron, 2015, vol. 71, # 38, p. 7073 - 7076]
[8]Singh, Rahulkumar Rajmani; Liu, Rai-Shung [Chemical Communications, 2017, vol. 53, # 33, p. 4593 - 4596]
[9]Zhang, Kaifan; Xu, Xiaoying; Zheng, Jiuan; Yao, Hequan; Huang, Yue; Lin, Aijun [Organic Letters, 2017, vol. 19, # 10, p. 2596 - 2599]
[10]Qiao, Chang; Liu, Xiao-Fang; Fu, Hong-Chen; Yang, Hao-Peng; Zhang, Zhi-Bo; He, Liang-Nian [Chemistry - An Asian Journal, 2018, vol. 13, # 18, p. 2664 - 2670]
[11]Xia, Qinqin; Bao, Xiaodong; Sun, Chuchu; Wu, Di; Rong, Xiaona; Liu, Zhiguo; Gu, Yugui; Zhou, Jianmin; Liang, Guang [European Journal of Medicinal Chemistry, 2018, vol. 160, p. 120 - 132]
[12]Dai, Zhen; Li, Songhua; Li, Yunyi; Feng, Lei; Ma, Chen [Tetrahedron, 2019, vol. 75, # 13, p. 2012 - 2017]
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5
[ 3420-02-8 ]
[ 86911-82-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 4h;	12 Preparation of 6-methylindoline To a mixture of 6-methyl-1H-indole (2.0 g, 15.25 mmol) in AcOH (20 mL) at 0 °C, was added NaBH3CN (1.9 g, 30.5 mmol). The reaction mixture was stirred at RT for 4 h. LC- MS showed the reaction was complete, it was neutralized by NaOH, extracted with EtOAc, the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 6-methylindoline as a a colorless oil (2.09 g, quantitative yield). LC-MS (ESI): m/z (M+1)+ = 134.15.
98%	With tetrahydroxydiboron; palladium on activated carbon In 2,2,2-trifluoroethanol; water at 40℃; for 24h; Schlenk technique;
90%	With sodium cyanoborohydride In acetic acid at 20℃; for 4h;

69%	With potassium <i>tert</i>-butylate; hydrogen; C₃₁H₃₁BrMnNO₂P₂ In toluene at 100℃; for 36h; Autoclave; chemoselective reaction;
51%	With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 2h;	Preparation 31 : 6-Methyl-2,3-dihydro-1 H-indole6-Methyl indole (0.50 g, 3.8 mmol) was dissolved in glacial acetic acid (19.1 mL) and cooled to 0 °C. Sodium cyanoborohydride (0.48 g, 7.6 mmol) was added portionwise and the mixture warmed to ambient temperature and stirred for 2 h. The reaction was diluted with water (8.0 mL), made alkaline with 40% aqueous NaOH and extracted with EtOAc (3 x 10 mL). The combined organic extracts were washed with brine (3 x 30 mL), dried over sodium sulfate, filtered and concentrated. Purification by column chromatography on silica gel (gradient elution, 0-100% EtOAc/petrol), gave the title compound (0.256 g, 51 %) as a purple oil. 1H NMR (Me-d3- OD): 6.96 (1 H, d), 6.53 (2H, d), 3.44 (2H, t), 2.94 (2H, t), 2.23 (3H, s).
51%	With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 2h;
	With sodium cyanoborohydride; acetic acid at 5℃; for 1h;
	With trimethylamine-borane
	Stage #1: 6-methylindole With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 1h; Stage #2: With water; sodium hydrogencarbonate at 0℃;	10 Preparation Example 10 1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-6-methyl-1H-indole [Show Image] To a solution of 6-methyl-1H-indole (2 g) in acetic acid (50 mL) was added sodium cyanoborohydride (2.4 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution with ice-cooling, and the resulting mixture was extracted twice with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 5/1-1/1) to give 6-methyl-2,3-dihydro-1H-indole (1.53 g). A mixture of 6-methyl-2,3-dihydro-1H-indole (1.5 g), D-glucose (2.1 g) and water (0.2 mL) was stirred at 100°C for 2 hour, and then the reaction mixtue was cooled to room temperature. To the residue was added acetic anhydride (9.2 g), N, N-dimethylaminopyridine (1.4 g) and pyridine (20 mL) , and the resulting mixture was stirred at room temperature for 2 hour. The reaction mixture was poured into ice-water. The resulting mixture was acidified with 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1-1/3) to give 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-methyl-2,3-dihydro-1H-indole (3.55 g). To a solution of 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-methyl-2,3-dihydro-1H-indole (2.9 g) in 1,4-dioxane (100 mL) was added, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.7 g) at room temperature, and the resulting mixture was stirred for 1 hour. The reaction mixture was poured into ice-water. To the resulting mixture was added a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 2/1-1/2) to give the title compound (2.42 g). 1H-NMR (CDCl3) δ ppm: 1.69 (3H, s), 2.04 (3H, s), 2.08 (3H, s), 2.09 (3H, s), 2.49 (3H, s), 3.95-4.05 (1H, m), 4.16 (1H, dd, J=12.4Hz, 2.4Hz), 4.3 (1H, dd, J=12.5Hz, 4.8Hz), 5.25-5.35 (1H, m), 5.4-5.5 (1H, m), 5.5-5.65 (2H, m) , 6.45-6.55(1H, m) , 6.95-7.05(1H, m) , 7.15 (1H, d, J=3.4Hz), 7.2 (1H, br s), 7.47 (1H, d, J=8.2Hz).
	With sodium cyanoborohydride; acetic acid at 0 - 20℃; Inert atmosphere;
	With sodium cyanoborohydride; acetic acid at 20℃;
	With sodium cyanoborohydride; acetic acid at 10 - 20℃; for 4h;
	With sodium cyanoborohydride; acetic acid at 20℃;
94 %Chromat.	With ammonia borane; C₅₂H₆₄N₁₂Pd₂S₄⁽²⁺⁾*2F₆P^(1-) In dodecane; toluene at 100℃; for 15h; Schlenk technique; Inert atmosphere; regioselective reaction;
	With sodium cyanoborohydride; acetic acid at 0℃; for 12h;
	With sodium cyanoborohydride; acetic acid at 20℃;

Reference： [1]Current Patent Assignee: REMEDY PLAN - WO2019/213570, 2019, A1 Location in patent: Paragraph 0331; 0688-0690
[2]Zhou, Xiao-Yu; Chen, Xia [Organic and Biomolecular Chemistry, 2021, vol. 19, # 3, p. 548 - 551]
[3]Kumar, Yatendra; Florvall, Lennart [Synthetic Communications, 1983, vol. 13, # 6, p. 489 - 494]
[4]Borghs, Jannik C.; Rueping, Magnus; Zubar, Viktoriia [Organic Letters, 2020]
[5]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - WO2012/143726, 2012, A1 Location in patent: Page/Page column 129
[6]Chessari, Gianni; Buck, Ildiko M.; Day, James E. H.; Day, Philip J.; Iqbal, Aman; Johnson, Christopher N.; Lewis, Edward J.; Martins, Vanessa; Miller, Darcey; Reader, Michael; Rees, David C.; Rich, Sharna J.; Tamanini, Emiliano; Vitorino, Marc; Ward, George A.; Williams, Pamela A.; Williams, Glyn; Wilsher, Nicola E.; Woolford, Alison J.-A. [Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6574 - 6588]
[7]Kamiya, Shoji; Shirahase, Hiroaki; Yoshimi, Akihisa; Nakamura, Shohei; Kanda, Mamoru; Matsui, Hiroshi; Kasai, Masayasu; Takahashi, Kenji; Kurahashi, Kazuyoshi [Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 6, p. 817 - 827]
[8]Zhao, He; Thurkauf, Andrew; He, Xiaoshu; Hodgetts, Kevin; Zhang, Xiaoyan; Rachwal, Stanislaw; Kover, Renata X.; Hutchison, Alan; Peterson, John; Kieltyka, Andrzej; Brodbeck, Robbin; Primus, Renee; Wasley, Jan W.F. [Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 21, p. 3105 - 3109]
[9]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - EP1803729, 2007, A1 Location in patent: Page/Page column 19-20
[10]Location in patent: experimental part Yao, Chun-Hsu; Song, Jen-Shin; Chen, Chiung-Tong; Yeh, Teng-Kuang; Hung, Ming-Shiu; Chang, Chih-Chun; Liu, Yu-Wei; Yuan, Mao-Chia; Hsieh, Chieh-Jui; Huang, Chung-Yu; Wang, Min-Hsien; Chiu, Ching-Hui; Hsieh, Tsung-Chih; Wu, Szu-Huei; Hsiao, Wen-Chi; Chu, Kuang-Feng; Tsai, Chi-Hui; Chao, Yu-Sheng; Lee, Jinq-Chyi [Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 166 - 178]
[11]Calderon, Felix; Vidal-Mas, Jaume; Burrows, Jeremy; De La Rosa, Juan Carlos; Jimenez-Diaz, Maria Belen; Mulet, Teresa; Prats, Sara; Solana, Jorge; Witty, Michael; Gamo, Francisco Javier; Fernandez, Esther [ACS Medicinal Chemistry Letters, 2012, vol. 3, # 5, p. 373 - 377]
[12]Jiang, Xue; Wang, Chao; Wei, Yawen; Xue, Dong; Liu, Zhaotie; Xiao, Jianliang [Chemistry - A European Journal, 2014, vol. 20, # 1, p. 58 - 63]
[13]Huang, Honggui; Yu, Menglin; Su, Xiaolong; Guo, Peng; Zhao, Jia; Zhou, Jiabing; Li, Yi [Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2425 - 2437]
[14]Jia, Wei-Guo; Gao, Li-Li; Wang, Zhi-Bao; Wang, Jing-Jing; Sheng, En-Hong; Han, Ying-Feng [Organometallics, 2020, vol. 39, # 10, p. 1790 - 1798]
[15]Xie, Guilin; Zhao, Yuhan; Cai, Changqun; Deng, Guo-Jun; Gong, Hang [Organic Letters, 2021, vol. 23, # 2, p. 410 - 415]
[16]Lu, Jiamin; Xu, Ruigang; Zeng, Haixia; Zhong, Guofu; Wang, Meifang; Ni, Zhigang; Zeng, Xiaofei [Organic Letters, 2021, vol. 23, # 9, p. 3426 - 3431]

6
[ 3420-02-8 ]
[ 68-12-2 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
94%		Example 4; 1. Synthesis of indole derivatives; 1) Synthesis of 3-cyanoindole derivatives; [Show Image] Nine objective compounds were prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-6-ether in dimethyl sulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order (the following Table 2). In addition, XO-CH172 and XO-CH183 (R is a 2-methyl group or a 5-methoxy group, respectively) were prepared from the step (2) using the corresponding aldehydes purchased.; 1) Synthesis of XO-CH200; XO-CH180 Under an argon atmosphere, 6-methylindole (1.004 g, 7. 62 mmol) was dissolved in dimethylformamide (10 mL), and to the solution was added phosphorus oxychloride (2 mL) under ice-cooling. The mixture was stirred for 1.5 hours at room temperature. To the reaction mixture was added dropwise an aqueous sodium hydroxide solution (5g/15mL) under ice-cooling. The mixture was heated for reflux for 1.5 hours. To the reaction mixture was added water under ice-cooling, and the mixture was adjusted to pH3 with concentrated hydrochloric acid. The solid was collected by filtration and dried at 60C under reduced pressure to give XO-CH180 as a pale brown solid (1.14 g, 94% yield).
89.38%		Add 30 mL of N,N-dimethylformamide (DMF) to a 250 mL three-necked flask, cool to below 0 C, and slowly add phosphorus oxychloride (6.30 mL, 67 mmol). After the addition is complete, let stand at room temperature and continue to stir. After 30 min, 25 mL of 6-methyl-1H-indole (II-3, 8.00 g, 61 mmol) in DMF was added dropwise in an ice bath. The temperature was controlled below 10 C. After the addition was completed, the temperature was raised to 35 C and stirred for 1 h.The reaction was monitored by TLC. After the reaction was completed, the reaction was quenched by adding 60 g of crushed ice under ice cooling, and then slowly added dropwise.1mol/L NaOH solution, adjust pH=89, and control the temperature in the dropping process to not exceed 40C. After the addition is completed, the mixture is heated to reflux for 1 hour.Stirring was carried out, cooled to room temperature, 55 mL of water was added dropwise, filtered, and the filter cake was washed with water until neutral. After drying, 8.67 g of a yellow solid was obtained.III-3, 89.38%.
79%		General procedure: The Vilsmeier-Haack reagent was prepared by adding POCl3 (60 mmol, 6 mL) dropwise to ice-cold dry DMF (30 mL) whilst stirring. The mixture was then stirred for 10-15 min at 0 C. Compound 3b or 3e (10 mmol) was added as a solution in DMF (5 mL) to the above Vilsmeier-Haack reagent. The stirred mixture was then heated at 35 C for 1 h. After cooling, ice water (6 mL) and a 30% aqueous solution of NaOH (13 mL) were added successively, and the mixture was heated at reflux for 20 min and allowed to cool. The mixture was extracted with CH2Cl2 (20 mL*3). The extracts were dried over Na2SO4, evaporated under reduced pressure to remove the solvent, and the crude product was purified by flash column chromatography using 15-25% acetone/petroleum ether (60-90 C) as eluent to give the corresponding intermediate compound 4b or 4e, respectively.

With sodium hydroxide; In water;

6-Methyl indole-3-carboxaldehyde Phosphorus oxychoride (3.2 ml, 34.3 mmol) was added dropwise to dimethyl formamide (26 ml) over ten minutes at ~5 C. To this solution was added a dimethyl formamide (32 ml) solution of 6-methylindole (3.307 g, 25.2 mmol) over 10 minutes. The mixture was slowly warmed to ambient temperature, then heated to 50 C. for four hours. The mixture was cooled to ambient temperature, then poured onto ice (500 g). The aqueous solution was left to stand for 16 hours. Sodium hydroxide (6.0 g) was dissolved in water (22 ml) and added dropwise to the brown solution. The resultant yellow precipitate was boiled and filtered hot. It was left to cool to room temperature, then to 5 C. The precipitate was filtered off and washed with water (800 ml), dried at the pump, then further dried in vacuo at 50 C. for 16 hours to yield a yellow solid.

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 5696 - 5705
[2]Patent: EP1932833,2008,A1 .Location in patent: Page/Page column 15; 19
[3]Chemical Biology and Drug Design,2011,vol. 78,p. 864 - 868
[4]Patent: CN109942545,2019,A .Location in patent: Paragraph 0076; 0078-0080
[5]European Journal of Medicinal Chemistry,2015,vol. 92,p. 776 - 783
[6]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305
[7]Patent: US5563147,1996,A
[8]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3780 - 3790
[9]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277
[10]Angewandte Chemie - International Edition,2013,vol. 52,p. 3250 - 3254
Angew. Chem.,2013,vol. 125,p. 3332 - 3336,5
[11]Organic Letters,2015,vol. 17,p. 3186 - 3189
[12]Chemistry - A European Journal,2015,vol. 21,p. 15104 - 15107
[13]Organic Letters,2017,vol. 19,p. 2502 - 2505
[14]Chemical Communications,2017,vol. 53,p. 5834 - 5837
[15]Organic Letters,2019,vol. 21,p. 2602 - 2605

7
[ 3420-02-8 ]
[ 3282-30-2 ]
[ 557763-02-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
72%	With triethylamine In dichloromethane at 0 - 20℃;
71%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique;

With dmap; triethylamine In dichloromethane

Reference： [1]Cornelia, Josep; Lu, Pengfel; Larrosa, Igor [Organic Letters, 2009, vol. 11, # 23, p. 5506 - 5509]
[2]Stuart, David R.; Villemure, Elisia; Fagnou, Keith [Journal of the American Chemical Society, 2007, vol. 129, # 40, p. 12072 - 12073]
[3]Iqbal, Saqib A.; Cid, Jessica; Procter, Richard J.; Uzelac, Marina; Yuan, Kang; Ingleson, Michael J. [Angewandte Chemie - International Edition, 2019, vol. 58, # 43, p. 15381 - 15385][Angew. Chem., 2019, vol. 131, p. 15525 - 15529,5]
[4]Komoda, Taichi; Shinoda, Yoshihiko; Nakatsuka, Shin-Ichi [Bioscience, Biotechnology and Biochemistry, 2003, vol. 67, # 3, p. 659 - 662]

8
[ 3420-02-8 ]
[ 59337-92-7 ]
3-(6-methyl-indole-1-sulfonyl)-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4445 - 4448

9
[ 3420-02-8 ]
[ 91-56-5 ]
3,3-bis(6-methyl-1H-indol-3-yl)indolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonium cerium(IV) nitrate In ethanol for 8h; sonication;
80%	With 60 wtpercent phosphotungstic acid supported on MCM-41 In tetrahydrofuran at 20℃; for 2.5h;	General procedure: Indoles (0.20mmol), isatins (0.10mmol), and 60 wt%PWA/MCM-41 catalyst (0.0050 g) were stirred in THF(0.3mL) at room temperature for 2.5 h and monitored byTLC. The product were purified by column chromatographyon silica gel using petroleum ether/ethyl acetate (20 : 1, 10 : 1,5 : 1, 2 : 1, 1 : 1) as the eluent. All compounds (3a-3o) werecharacterized by 1H and 13C NMR (400MHz) spectral analysis.The catalyst was separated from the reaction mixture bycentrifugalization, dried at 473K for 4 h after washing withethanol, then continued to be reused for the next reaction.

Reference： [1]Wang, Shun-Yi; Ji, Shun-Jun [Tetrahedron, 2006, vol. 62, # 7, p. 1527 - 1535]
[2]Xing, Liuzhuang; Hui, YongHai; Yang, Jinghui; Xing, Xuejian; Hou, Yadong; Wu, Yang; Fan, Kui; Wang, Wei [Journal of Chemistry, 2018, vol. 2018]

10
[ 3420-02-8 ]
[ 79-30-1 ]
[ 1002332-22-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 6-methylindole; methylmagnesium bromide In diethyl ether at 0 - 20℃; for 0.583333h; Stage #2: With zinc(II) chloride In diethyl ether at 20℃; for 0.25h; Stage #3: isobutyryl chloride With ammonium chloride more than 3 stages;	55 A solution of 6-methyl-1 H-indole (0.47 ml, 3.81 mmol) in Et2O (9.9 ml) was stirred at 0 0C under an atmosphere of argon. A solution of methyl magnesium bromide in Et2O (3M, 1.29 ml, 3.89 mmol) was added slowly to the reaction mixture over a period of 5 minutes. A slight exotherm was observed. The reaction mixture was stirred for 30 minutes allowing the reaction contents to warm to room temperature. After this time, zinc chloride in Et2O (1 M, 3.81 ml, 3.81 mmol) was added slowly to the reaction mixture. Green precipitate observed. The mixture was stirred at room temperature for a further 15 minutes. After this time, 2-methylpropanoyl chloride (0.40 ml, 3.81 mmol) was added to the reaction mixture. The mixture was stirred for 15 minutes at room temperature. The reaction was monitored by LC-MS. The reaction was quenched by the dropwise addition of saturated ammonium chloride (10 ml). The organics were extracted with EtOAc, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an orange solid. The crude product was recrystallized from Et2O to give a white solid, 1-[2-(ethenylamino)-4- methylphenyl]-3-methyl-2-butanone (0.43 g, 56%). LCMS Rt = 2.64 min, [M+H] 202, 203.
	Stage #1: 6-methylindole With methylmagnesium bromide In diethyl ether for 0.333333h; Stage #2: With zinc(II) chloride In diethyl ether for 0.5h; Stage #3: isobutyryl chloride In diethyl ether Further stages.;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/6790, 2008, A1 Location in patent: Page/Page column 31
[2]Hall, Adrian; Billinton, Andy; Brown, Susan H.; Chowdhury, Anita; Giblin, Gerard M.P.; Goldsmith, Paul; Hurst, David N.; Naylor, Alan; Patel, Sadhana; Scoccitti, Tiziana; Theobald, Pamela J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2684 - 2690]

11
[ 3420-02-8 ]
[ 209920-43-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2734 - 2737
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316
[3]Patent: WO2009/125923,2009,A2

12
[ 3420-02-8 ]
[ 40064-34-4 ]
[ 139774-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; ethyl acetate;	EXAMPLE 14 (INTERMEDIATES FOR METHOD) 3-[1-[2-[3-(2-propyl)-2-imidazolidinon-1-yl]ethyl]-4-piperidyl]-6-methyl-1H-indole, 14a To a solution of potassium hydroxide (16 g) in methanol were added at 5 C. 4-piperidone hydrate hydrochloride (30 g) and a solution of 6-methyl-1H-indole (10 g) in methanol (50 ml). The mixture was refluxed for 16 hours. After cooling precipitated inorganic salts were filtered off. Methanol was evaporated and the remaining oil was dissolved in ethyl acetate (200 ml) and subsequently washed with brine (2*100 ml). After drying (anh. MgSO4) the solvent was evaporated leaving 15 g of crude 6-methyl-3-(1,2,3,6-tetrahydro-4-pyridyl)-1H-indole, which was used without further purification.
		EXAMPLE 30 6-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 3.0 gm (28.0 mMol) 6-methyl-1H-indole and 7.04 gm (45.7 mMol) <strong>[40064-34-4]4-piperidone hydrochloride monohydrate</strong>, 1.1 gm (22%) of the title compound were recovered as a tan powder. EA: Calculated for: C16 H16 N2: Theory: C, 79.21; H, 7.60; N, 13.20. Found: C, 78.94; H, 7.67; N, 12.93.
		EXAMPLE 30 6-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 3.0 gm (28.0 mMol) 6-methyl-1H-indole and 7.04 gm (45.7 mMol) <strong>[40064-34-4]4-piperidone hydrochloride monohydrate</strong>, 1.1 gm (22%) of the title compound were recovered as a tan powder. EA: Calculated for: C16H16N2: Theory: C, 79.21; H, 7.60; N,

Reference： [1]Patent: US5216001,1993,A
[2]Patent: US5846982,1998,A
[3]Patent: EP812826,1997,A1

13
[ 1075-26-9 ]
[ 3420-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	palladium on charcoal; In ethanol; chloroform; acetic acid;	6-Methyl indole 6-hydroxymethyl indole (6.135 g, 41.69 mmol) was dissolved in ethanol (70 ml). 10% Palladium on charcoal (0.610 g) was suspended in acetic acid (70 ml) and added to the ethanol (70 ml) solution. The mixture was placed on the high pressure hydrogenator at 60 psi. After 20 hours, the mixture was filtered through Celite and the resulting solution concentrated in vacuo. The mixture was purified by flash chromatography using chloroform as solvent to yield a colourless oil.

Reference： [1]Patent: US5563147,1996,A

14
[ 3420-02-8 ]
[ 40064-34-4 ]
[ 180161-02-8 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 31 7-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 2.0 gm (15.0 mMol) 6-methyl-1H-indole and 4.69 gm (30.0 mMol) <strong>[40064-34-4]4-piperidone hydrochloride monohydrate</strong>, 2.2 gm (68%) of the title compound were recovered as a yellow solid. HRMS: Calculated for: C16 H16 N2: Theory: m/e=213.139174. Found: m/e=213.141200.
		EXAMPLE 31 7-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 2.0 gm (15.0 mMol) 6-methyl-1H-indole and 4.69 gm (30.0 mMol) <strong>[40064-34-4]4-piperidone hydrochloride monohydrate</strong>, 2.2 gm (68%) of the title compound were recovered as a yellow solid. HRMS: Calculated for: C16H16N2: Theory: m/e = 213.139174. Found: m/e = 213.141200.

Reference： [1]Patent: US5846982,1998,A
[2]Patent: EP812826,1997,A1

15
[ 3420-02-8 ]
[ 125664-95-1 ]
C₂₂H₂₈N₂O₃S [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12857 - 12869

16
[ 3420-02-8 ]
[ 121-51-7 ]
[ 1194041-99-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1.5h;
88%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 40℃; Irradiation;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;

	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1h;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1.5h;	7 Compound 22 The preparation method is as follows: 6-methylindole weighed (1mmol), m-nitrobenzenesulfonyl chloride (1.2mmol), Sodium hydroxide (1.8 mmol) and TEBA (0.1 mmol) in a 50 mL flask. Add dichloromethane (5 mL), react at room temperature for 1.5 h, and trace the reaction to complete reaction by TLC. The reaction was quenched with water (10 mL). dry over anhydrous sodium sulfate, concentration under reduced pressure gave compound 22 which was used directly to afford compound 7 without isolation

Reference： [1]Location in patent: scheme or table Xu, Hui; Wang, Yangyang [Chinese Journal of Chemistry, 2010, vol. 28, # 1, p. 125 - 127]
[2]Location in patent: experimental part Fan, Ling-Ling; Liu, Wu-Qing; Xu, Hui; Yang, Liu-Meng; Lv, Min; Zheng, Yong-Tang [Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 8, p. 797 - 800]
[3]Ran, Jun-Qiang; Huang, Ning; Xu, Hui; Yang, Liu-Meng; Lv, Min; Zheng, Yong-Tang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3534 - 3536]
[4]Location in patent: scheme or table Xu, Hui; Wang, Yang-Yang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7274 - 7277]
[5]Che, Zhiping; Zhang, Shaoyong; Shao, Yonghua; Fan, Lingling; Xu, Hui; Yu, Xiang; Zhi, Xiaoyan; Yao, Xiaojun; Zhang, Rui [Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705]
[6]Current Patent Assignee: HENAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105061287, 2018, B Location in patent: Paragraph 0130-0134

17
benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate [ No CAS ]
[ 3420-02-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogen In ethanol; water at 25℃; for 18h;	2 a mixture of benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate (13 mmol), 5% palladium (0.84 g), water (4 mL) and ethanol (40 mL) is hydrogenated under 50 psi for 18 hours at 25° C. The catalyst is eliminated by filtration on celite and the solid is washed with ethanol. The filtrate obtained is evaporated under vacuum and the residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 2/1) in order to produce 6-methylindole with a yield of 74%.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; COMMUNITY GRENOBLE ALPES UNIVERSITY - US2010/144726, 2010, A1 Location in patent: Page/Page column 47

18
[ 3420-02-8 ]
[ 98-59-9 ]
6-methyl-1-tosyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1.5h;
80%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 16h;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;

	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1h;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1h;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃;
	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 1.5h;	1 Compound 16 The preparation method is as follows: 6-Methyl indole (1 mmol), p-toluenesulfonyl chloride (1.2 mmol), sodium hydroxide (1.8 mmol) and TEBA (0.1 mmol) were weighed in a 50 mL flask, and dichloromethane (5 mL) was added. The reaction was carried out at room temperature for 1.5 h, and the reaction was completed by TLC. The reaction was quenched with water (10 mL), and extracted with dichloromethane (20 mL×3). The organic phase was combined and the organic phase was washed with saturated sodium chloride solution (10 mL). The sodium was dried and concentrated under reduced pressure to give compound 16 which was used directly for the preparation of compound 1 without isolation
	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 20℃; for 14h;
	Stage #1: 6-methylindole With sodium hydride In acetonitrile at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In acetonitrile at 0 - 20℃; for 4h;

Reference： [1]Location in patent: scheme or table Xu, Hui; Wang, Yangyang [Chinese Journal of Chemistry, 2010, vol. 28, # 1, p. 125 - 127]
[2]Jayaraman, Arumugam; Misal Castro, Luis C.; Fontaine, Frédéric-Georges [Organic Process Research and Development, 2018, vol. 22, # 11, p. 1489 - 1499]
[3]Ran, Jun-Qiang; Huang, Ning; Xu, Hui; Yang, Liu-Meng; Lv, Min; Zheng, Yong-Tang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3534 - 3536]
[4]Location in patent: scheme or table Xu, Hui; Wang, Yang-Yang [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7274 - 7277]
[5]Location in patent: experimental part Xu, Hui; Bin Yang, Wen; Wang, Qin [Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868]
[6]Che, Zhiping; Zhang, Shaoyong; Shao, Yonghua; Fan, Lingling; Xu, Hui; Yu, Xiang; Zhi, Xiaoyan; Yao, Xiaojun; Zhang, Rui [Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705]
[7]Current Patent Assignee: HENAN UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105061287, 2018, B Location in patent: Paragraph 0042-0046
[8]Qiang-Liu; Liu, Yu-Xiu; Song, Hong-Jian; Wang, Qing-Min [Advanced Synthesis and Catalysis, 2020, vol. 362, # 15, p. 3110 - 3115]
[9]Chen, Yong-Jia; Liu, Hua; Zhang, Shao-Yong; Li, Hu; Ma, Kun-Yuan; Liu, Ying-Qian; Yin, Xiao-Dan; Zhou, Rui; Yan, Yin-Fang; Wang, Ren-Xuan; He, Ying-Hui; Chu, Qing-Ru; Tang, Chen [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 4, p. 1259 - 1271]

19
[ 3420-02-8 ]
[ 100-39-0 ]
[ 1274877-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-methylindole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
	With potassium hydroxide In tetrahydrofuran at 0℃; for 24h;
	With potassium hydroxide In tetrahydrofuran at 0℃; for 24h;

	Stage #1: 6-methylindole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	General procedure for the synthesis of 1-benzyl-1H-indole 2:1 General procedure: Indole (1) (30 mmol, 1 equiv) was dissolved in DMF (30 mL) and the resulting solution was added KOH (6.7g, 120 mmol, 4 equiv) at 0 °C. The mixture was stirred for 20 min at 0 °C and benzyl bromide (4.3 mL, 36 mmol, 1.2 equiv) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 1h, before quenching the reaction by pouring it onto ice. The organic layer was diluted with EtOAc (30 mL) and separated from the aqueous one. The latter was extracted with EtOAc (3×30 mL). The combined organic layers were wash with water (20 mL) and brine (30 mL), were dried over MgSO4, filtered and concentrated in vacue to afford as yellow solid, which did not require further purification.
	Stage #1: 6-methylindole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere;
	With potassium hydroxide In dimethyl sulfoxide at 20℃;	2.1 Synthesis of N-benzyl indoles General procedure: A 50 mL round-bottomed flask was charged with substituted indoles (5 mmol), KOH (10.0 mmol), 20 mL of DMSO, and alkyl bromides (10.0 mmol).The reaction mixture was stirred at room temperature and monitored by TLC. Upon completion, the reaction mixture was quenched with water (20 mL). The mixture was extracted with ethyl acetate (3 × 30 mL). The combined organic phases were dried over anhydrous MgSO4. The product was purified by silica gel chromatography with petroleum ether/DCM.

Reference： [1]Liu, Qiang; Li, Gang; Yi, Hong; Wu, Pan; Liu, Jie; Lei, Aiwen [Chemistry - A European Journal, 2011, vol. 17, # 8, p. 2353 - 2357]
[2]Lang, Rui; Wu, Junliang; Shi, Lijun; Xia, Chungu; Li, Fuwei [Chemical Communications, 2011, vol. 47, # 46, p. 12553 - 12555]
[3]Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei [Chemical Communications, 2012, vol. 48, # 89, p. 11023 - 11025] Xing, Qi; Li, Pan; Lv, Hui; Lang, Rui; Xia, Chungu; Li, Fuwei [Chemical Communications, 2014, vol. 50, # 81, p. 12181 - 12184]
[4]Yang, Yan-Fang; Li, Lian-Hua; He, Yu-Tao; Luo, Jian-Yi; Liang, Yong-Min [Tetrahedron, 2014, vol. 70, # 3, p. 702 - 707]
[5]Yang, Youqing; Gao, Pan; Zhao, Yue; Shi, Zhuangzhi [Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 3966 - 3971][Angew. Chem., 2017, vol. 129, p. 4024 - 4029]
[6]Liu, Yuxia; Wang, Chao; Huang, Linjuan; Xue, Dong [Synlett, 2020, vol. 31, # 16, p. 1613 - 1618]

20
[ 3420-02-8 ]
[ 383-63-1 ]
3,3,3-trifluoro-2-hydroxy-2-(6-methyl-1H-indol-3-yl)-propionic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With C₇₈H₇₈N₁₂O₆ In tetrahydrofuran at -20℃; for 12h; Inert atmosphere; enantioselective reaction;	4.1.1 General procedure for the asymmetric Friedel-Crafts reaction of indoles with alkyl trifluoropyruvates General procedure: Under an argon atmosphere, indole (0.2 mmol, 23.2 mg) and catalyst L1 (0.01 mmol, 12.8 mg) were dissolved in 2 mL of THF at -20 °C. The mixture was stirred at -20 °C for 30 min. Ethyl 3,3,3-trifluoropyruvate (0.3 mmol) was then added. The mixture was stirred at -20 °C for 12 h and then progress was monitored by TLC. After the reaction was completed, the solvents were removed. Next, the crude product was purified by column chromatography (petroleum ether/ethyl acetate = 4:1).

Reference： [1]Han, Xin; Liu, Bin; Zhou, Hai-Bing; Dong, Chune [Tetrahedron Asymmetry, 2012, vol. 23, # 18-19, p. 1332 - 1337,6]

21
[ 1722-12-9 ]
[ 3420-02-8 ]
[ 1414866-82-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 0 - 130℃; for 24h; Inert atmosphere; Sealed tube;
78%	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h;

	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 100℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; Schlenk technique;	General procedure for synthesis of N-pyrimidyl indoles¹ General procedure: NaH(60% dispersion in mineral oil, 3.6 mmol) was added in portions at 0 °C to a stirred solution of indole (3.0 mmol) in DMF (10 mL). After stirring for 30 min at 0°C, chloropyrimidine(3.6 mmol) was added and the mixture was stirred at 130 °C for 4-24 h. Then,the reaction mixture was cooled to ambient temperature, poured into H2O(20 mL) and extracted with EtOAc (25 mL×2). The combined organic phase was dried over Na2SO4. After filtration and evaporation ofthe solvents under reduced pressure, the crude product was purified by column chromatography on silica gel to afford the corresponding product.
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h; Inert atmosphere;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h; Inert atmosphere; Schlenk technique;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 0 - 130℃; for 24h;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide; mineral oil at 130℃; for 24h; Inert atmosphere;
	Stage #1: 6-methylindole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 2-chloropyrimidine In N,N-dimethyl-formamide for 24h; Inert atmosphere; Schlenk technique; Reflux;

Reference： [1]Wu, Hongxiang; Liu, Tingting; Cui, Ming; Li, Yue; Jian, Junsheng; Wang, Hui; Zeng, Zhuo [Organic and Biomolecular Chemistry, 2017, vol. 15, # 3, p. 536 - 540]
[2]Shi, Jingjing; Zhou, Bing; Yang, Yaxi; Li, Yuanchao [Organic and Biomolecular Chemistry, 2012, vol. 10, # 45, p. 8953 - 8955]
[3]Gong, Binwei; Shi, Jingjing; Wang, Xiaowei; Yan, Yunnan; Li, Qiu; Meng, Yanqiu; Xu, H. Eric; Yi, Wei [Advanced Synthesis and Catalysis, 2014, vol. 356, # 1, p. 137 - 143]
[4]Shi, Jingjing; Zhao, Guanguan; Wang, Xiaowei; Xu, H. Eric; Yi, Wei [Organic and Biomolecular Chemistry, 2014, vol. 12, # 35, p. 6831 - 6836]
[5]Wang, Liang; Qu, Xing; Li, Zhan; Peng, Wang-Ming [Tetrahedron Letters, 2015, vol. 56, # 24, p. 3754 - 3757]
[6]Lv, Honggui; Xu, William L.; Lin, Kunhua; Shi, Jingjing; Yi, Wei [European Journal of Organic Chemistry, 2016, vol. 2016, # 34, p. 5637 - 5641]
[7]Zhu, Chuan; Song, Shengjin; Zhou, Lu; Wang, Ding-Xing; Feng, Chao; Loh, Teck-Peng [Chemical Communications, 2017, vol. 53, # 68, p. 9482 - 9485]
[8]Jiang, Cheng; Zheng, Zhao-Jing; Yu, Tian-Yang; Wei, Hao [Organic and Biomolecular Chemistry, 2018, vol. 16, # 39, p. 7174 - 7177]
[9]Lu, Ming-Zhu; Ding, Xin; Shao, Changdong; Hu, Zhengsong; Luo, Haiqing; Zhi, Sanjun; Hu, Huayou; Kan, Yuhe; Loh, Teck-Peng [Organic Letters, 2020, vol. 22, # 7, p. 2663 - 2668] Zhang, Dong; Fang, Zheng; Cai, Jinlin; Liu, Chengkou; He, Wei; Duan, Jindian; Qin, Ning; Yang, Zhao; Guo, Kai [Chemical Communications, 2020, vol. 56, # 58, p. 8119 - 8122]
[10]Dong, Lefeng; Li, Zhong; Liang, Junqing; Pang, Xiwen; Qin, Jiawei; Shao, Xusheng; Wang, Gangao; Xu, Xiaoyong [Organic Letters, 2021, vol. 23, # 14, p. 5545 - 5548]
[11]Zhang, Shang-Shi; Zheng, Yi-Chuan; Zhang, Zi-Wu; Chen, Shao-Yong; Xie, Hui; Shu, Bing; Song, Jia-Lin; Liu, Yan-Zhi; Zeng, Yao-Fu; Zhang, Luyong [Organic Letters, 2021, vol. 23, # 15, p. 5719 - 5723]
[12]Suzuki, Hirotsugu; Liao, Yumeng; Kawai, Yuya; Matsuda, Takanori [European Journal of Organic Chemistry, 2021, vol. 2021, # 35, p. 4938 - 4942]

22
[ 3420-02-8 ]
[ 1266617-35-9 ]
[ 1418209-94-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With gluconic acid In water at 110℃; for 11h; Green chemistry;	A typical procedure for ring-opening reaction of 2-butoxy-3, 4-dihydropyran 1a with indole: General procedure: In a typical reaction, gluconic acid aqueous solution (1.0 ml) was mixed with 1a (57.1 mg, 0.25 mmol) and indole (1a, 73.2 mg, 0.63 mmol) under air. The mixture was stirred for 11 hours at 110 °C. After reaction, the mixture was cooled to room temperature and the reaction mixture was extracted with a mixed solution composed of ethyl acetate and n-heptane (v/v = 2/1,6 ml × 3). And the desired product, 3a, was obtained by preparative TLC using a mixed solution of ethyl acetate and petro ether as eluting solvent (the ratio of ethyl acetate/petroether is 1/6). 79.4 mg, Yield = 82%.

Reference： [1]Yang, Jie; Zhou, Binghua; Li, Minghao; Gu, Yanlong [Tetrahedron, 2013, vol. 69, # 3, p. 1057 - 1064]

23
[ 3420-02-8 ]
[ 66715-65-9 ]
[ 1429474-14-5 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: pyridine-2-sulfonyl chloride at 20℃; Inert atmosphere;
57%	Stage #1: 6-methylindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: pyridine-2-sulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	2 6-Methyl-1-(pyridin-2-ylsulfonyl)-1H-indole (44) Example 2 6-Methyl-1-(pyridin-2-ylsulfonyl)-1H-indole (44) 6-Methylindole (42) (7.34 g, 56.0 mmol) was added in portions to a mixture of sodium hydride (3.36 g, 84.0 mmol) in THF (80 mL) at 0° C. After 15 min, pyridine-2-sulfonyl chloride (43) (10.0 g, 56.0 mmol) was added, and the reaction was allowed to warm to rt and stirred overnight under N2. The reaction mixture was then quenched with ice water and extracted with EtOAc. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 40% EtOAc-hexanes to provide 8.8 g (57%) of product 44 as a brown gum. 1H NMR (300 MHz, CDCl3) δ 2.44 (s, 3H), 6.62 (dd, J=1, 4 Hz, 1H), 7.03-7.06 (m, 1H), 7.41 (d, J=8 Hz, 1H), 7.41-7.45 (m, 1H), 7.59 (d, J=4 Hz, 1H), 7.79-7.81 (m, 1H), 7.84-7.90 (m, 1H), 8.10 (dt, J=1, 8 Hz, 1H), 8.58-8.60 (m, 1H). LC-MS (CI): m/z 273.0 [(M+H)+ C14H12N2O2S requires 272.06].

Reference： [1]Nuth, Manunya; Guan, Hancheng; Zhukovskaya, Natalia; Saw, Yih Ling; Ricciardi, Robert P. [Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3235 - 3246]
[2]Current Patent Assignee: UNIVERSITY OF PENNSYLVANIA - US2014/343114, 2014, A1 Location in patent: Paragraph 0274

24
[ 100-42-5 ]
[ 3420-02-8 ]
[ 1383935-51-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: styrene With iodine; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione at 80 - 85℃; for 2h; Sealed tube; Stage #2: 6-methylindole In dimethyl sulfoxide at 20℃; for 5h; Sealed tube;	3.22 4.2 General procedure for synthesis of 3 (3aa as an example) General procedure: A sealed tube was charged with styrene (1a) (52mg, 0.5mmol), IBX (140mg, 0.5mmol), and iodine (189.5mg, 0.75mmol) at room temperature, and dried solvent DMSO (3mL) was then added. The resulting mixture was stirred at 80-85°C for 2h, after disappearance of the reactant (monitored by TLC), then added N-methylindole 2a (134mg, 1.0mmol) at room temperature for another 5h. After the reaction completed, then added 50mL water to the mixture, extracted with EtOAc three times (3×50mL). The extract was washed with 10% Na2S2O3 solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=10:1) to afford the desired product 3aa as a brown solid (66% yield).

Reference： [1]Jia, Feng-Cheng; Zhu, Yan-Ping; Liu, Mei-Cai; Lian, Mi; Gao, Qing-He; Cai, Qun; Wu, An-Xin [Tetrahedron, 2013, vol. 69, # 34, p. 7038 - 7044]

25
[ 3420-02-8 ]
[ 75702-97-5 ]
[ 1543023-45-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	With trifluorormethanesulfonic acid; sodium sulfate In neat (no solvent) at 115℃; for 12h; Sealed tube; Inert atmosphere;	3,3'-(1-Cyclopropyl-2,2,2-trifluoroethane-1,1-diyl)bis(6-methyl-1H-indole)(3j) General procedure: Trifluoromethyl ketone (0.3mmol),trifluoromethanesulfonicacid (9mg, 0.06mmol) were added to a dry sealed tube charged with indole(0.9mmol) and sodium sulphate anhydrous (12.8mg, 0.09mmol) under argon. Thereaction mixture was stirred at 115°C for 12h. After the reaction was completed, the mixture was purifiedby column chromatography on silica gel with hexanes/ethyl acetate as eluent.The desired product was obtained as white or pale yellow solid. Isolatedyield: 68%. White solid. M.P.: 190-192oC. 1H NMR (400MHz, CDCl3) δ 8.06 (s, 2 H), 7.37 (d, J = 1.6 Hz, 2 H), 7.09(s, 2 H), 6.69 (d, J = 8.4 Hz, 2 H), 6.52 (d, J = 8.4 Hz, 2 H),2.32 (s, 6 H), 1.99-1.91 (m, 1 H), 0.56-0.52(m, 2 H), 0.26-0.23 (m, 2 H) 19FNMR (375 MHz, CDCl3) δ -69.69 (s, 3 F); 13C NMR(100.7 MHz, CDCl3) δ 136.4, 131.3, 128.6 (q, J = 285.5 Hz),125.0, 123.9, 121.2, 121.1 (q, J = 1.1 Hz), 110.8 (q, J = 1.5 Hz),50.2 (q, J = 25.3 Hz), 21.4, 15.3 (q, J = 2.2 Hz), 2.1 ppm. IR (KBr):ν = 3415, 2920, 1627, 1540, 1457, 1396, 1340, 1256, 1239, 1175, 1150,1130, 1109, 1076, 1031, 996, 952, 884, 800 cm-1. MS (EI): m/z (%)382 (M , 100), 354, 313, 251, 225,157, 144. HRMS: Calculated for C23H21F3N2: 382.1657; Found: 382.1653
68%	With trifluorormethanesulfonic acid; sodium sulfate In neat (no solvent) at 115℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry;	Representative procedure ofthe reaction of indole with 1 General procedure: Trifluoromethylketone (0.3mmol),trifluoromethanesulfonic acid (9mg, 0.06mmol) were added to a dry sealedtube charged with indole (0.9mmol) and sodium sulphate anhydrous(12.8mg, 0.09mmol) under argon. The reaction mixture was stirred at 115°C for12h. After the reaction was completed, the mixture was purifiedby column chromatography on silica gel with hexanes/ethyl acetate as eluent.The desired product was obtained as white or pale yellow solid.

Reference： [1]Wang, Yi; Yuan; Xing, Chun-Hui; Lu, Long [Tetrahedron Letters, 2014, vol. 55, # 5, p. 1045 - 1048]
[2]Wang, Yi; Yuan, Yu; Xing, Chun-Hui; Lu, Long [Tetrahedron Letters, 2014, vol. 55, # 5, p. 1045 - 1048]

26
[ 3420-02-8 ]
[ 62005-48-5 ]
[ 1629189-24-7 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3822 - 3830

27
[ 3420-02-8 ]
[ 34157-83-0 ]
(2R,4aS,6aS,12bR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-8-(6-methyl-1H-indol-3-yl)-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With aluminium(III) chloride hexahydrate In dichloromethane at 20℃; for 3h; Sealed tube;	3.3. General Procedure for the Friedel-Crafts Alkylation General procedure: Celastrol (2a, 0.222 mmol, 100 mg) and indole (3a, 0.266 mmol, 31 mg) were dissolved in dichloromethane (DCM, 2 mL) in a 10 mL closed tube. After intensive stirring at room temperature,the metal catalyst AlCl3.6H2O (5 mol %, 2.7 mg) was added to the solution and the reaction mixturewas stirred for 3 h. When the reaction was finished, pure water (20 mL) was added to stop the reaction and subsequently the aqueous phase was separated and extracted with ethyl acetate (20 mL) three times. The organic layers were combined and dried with anhydrous sodium sulfate. The solvent was removed in vacuo, giving a crude mixture which was purified by flash chromatography on silica column (hexane/ethyl acetate/AcOH = 4:1:0.005) to give the pure products 3a-3q, 1a2b, 1a2c.NMR spectra for all compounds can be found in Supplementary Materials.
	With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h;

Reference： [1]Zhu, Yi; Chen, Ziwen; Huang, Zhenfei; Yan, Siwei; Li, Zhuoer; Zhou, Hu; Zhang, Xiaokun; Su, Ying; Zeng, Zhiping [Molecules, 2017, vol. 22, # 5]
[2]Tang, Kaiyong; Huang, Jinwen; Pan, Junfang; Zhang, Xuan; Lu, Wei [RSC Advances, 2015, vol. 5, # 25, p. 19620 - 19623]

28
[ 3420-02-8 ]
[ 623-47-2 ]
ethyl 3,3-bis(6-methyl-1H-indol-3-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 6-methylindole With gallium tris(dodecyl sulfate) In water for 0.166667h; Green chemistry; Stage #2: propynoic acid ethyl ester In water at 50℃; for 18h; Green chemistry; regioselective reaction;	General synthesis of ethyl 3,3-di(1H-indol-3-yl)propanoate (3a) General procedure: Gallium tris(dodecylsulfate) (0.05 mmol), indole (1 mmol) and water (25 mL) was added into a 100 mL screw capped tube. After vigorous stirring for 10 minutes, ethyl propiolate (1.2 mmol) was added, followed by screwing and heating to 70°C for 18 hours. After completion of reaction (as monitored by TLC), a little amount of sodium chloride was introduced, then the reaction mixture was extracted with ethyl acetate. Dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to leave the crude product which was purified by chromatography over silica gel.
95%	With gallium(III) dodecyl sulfate In water at 50℃; for 18h;	General procedure for the reaction of indole derivatives and propiolates General procedure: To a mixture of Ga(DS)3 (0.05 mmol), indole derivative (1.0 mmol) and propiolate (1.0 mmol) in 10 mLwater. The mixture was stirred at desired temperature for an appropriate time. After cooling to rt, brinewas added and the product was extracted by EtOAc. The organic layer was separated, dried over anhydrous Na2SO4 and evaporated. The residue was purified by column chromatography, usingacetone/petroleum ether as the eluent.

Reference： [1]An, Li-Tao; Cai, Jing-Jing; Pan, Xiang-Qiang; Chen, Tang-Ming; Zou, Jian-Ping; Zhang, Wei [Tetrahedron Letters, 2015, vol. 56, # 26, p. 3996 - 3998]
[2]Zhu, Xun; Zhou, Xiuqin; Xiang, Dongsheng [Heterocycles, 2015, vol. 91, # 8, p. 1637 - 1644]

29
[ 3420-02-8 ]
methyl 1-acetyl-2-(p-tolyl)cyclopropane-1-carboxylate [ No CAS ]
methyl 1,7-dimethyl-4-(p-tolyl)-4,9-dihydro-3H-carbazole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With toluene-4-sulfonic acid In ethanol at 60℃; for 0.333333h; regioselective reaction;	16 General procedure for the reaction between DACS and indoles General procedure: In a typical reaction, DAC (0.20 mmol) was mixed with indole (0.20 mmol) and PTSA (10 mol%) in ethanol (1.0 mL). The mixture was then stirred at 60°C for 20 min. After reaction, the mixture was cooled to room temperature, and the product was obtained by isolation with preparative TLC (eluting solution: petroleum ether/ethyl acetate=5/1 (v/v)). Tests for substrate scope were all performed with an analogous procedure. Large scale synthesis was also performed in a similar procedure. The product was isolated by silica column chromatography (eluting solution: petroleum ether/ethyl acetate=8/1 (v/v)).

Reference： [1]Liu, Changhui; Zhou, Li; Huang, Wenbo; Wang, Man; Gu, Yanlong [Tetrahedron, 2016, vol. 72, # 4, p. 563 - 570]

30
[ 3420-02-8 ]
[ 5649-36-5 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9480 - 9497
[2]Organic Letters,2019,vol. 21,p. 14 - 17
[3]Organic Letters,2021,vol. 23,p. 2212 - 2216

31
[ 3420-02-8 ]
C₁₈H₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bismuth(III) chloride In dichloromethane at 20℃; for 6h;	2. General procedure for the synthesis of 2,3-dihydro-2,3'-bisindoles 2 General procedure: A mixture of N-free indole derivatives 1 (0.5 mmol), BiCl3 (0.5 mmol) in dry CH2Cl2 was stirred for 6 h at rt. Then, the reaction was diluted with ethyl acetate (20 mL), washed with saturated aqueous NaHCO3 solution and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. After concentrated, the residue was purified by flash column chromatography (silica gel, hexane/EtOAc) to afford the desired products 2. Physical and spectroscopic data follow.

Reference： [1]Guo, Tao; Han, Shu-Lei; Liu, Ying-Chao; Liu, Yu; Liu, Hong-Min [Tetrahedron Letters, 2016, vol. 57, # 10, p. 1097 - 1099]

32
[ 3420-02-8 ]
[ 591-50-4 ]
6-methyl-3-(phenylselanyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium phosphate dodecahydrate; selenium; copper(II) oxide In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction;
86.5%	With selenium; potassium phosphate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 15h;	10 Example 10 To the organic solvent DMS0 in the reaction vessel at room temperature, a compound of the above formula (II) Compounds, elemental Se, CuO powder and K3P04 · 12H20. Wherein the molar ratio of the compound of the formula (II) to the compound of the formula (III) is 1: 2, the molar ratio of the compound of the formula (Π) to the element Se is 1: 2, the molar ratio of the compound of the formula (II) to CuO is 1: 0.3 , The molar ratio of the compound of formula (II) to K3P04 · 12H20 was 1: 4, and then the temperature was raised to 80 ° C by stirring in an air atmosphere and the reaction was carried out for 15 hours. After the post-treatment, the product (I) as a yellow solid was obtained with a yield of 86.5% and a purity of 98.6% (HPLC)

Reference： [1]Luo, Dongping; Wu, Ge; Yang, Hang; Liu, Miaochang; Gao, Wenxia; Huang, Xiaobo; Chen, Jiuxi; Wu, Huayue [Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4485 - 4493]
[2]Current Patent Assignee: WENZHOU UNIVERSITY - CN104387311, 2016, B Location in patent: Paragraph 0116-0119

33
[ 3420-02-8 ]
[ 257-07-8 ]
2-(2-(bis(6-methyl-1H-indol-3-yl)methyl)phenoxy)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With trifluoroacetic acid In dichloromethane at 20℃; for 5h;	General procedure for the double aza-Friedel-Crafts reaction in DCM (Scheme 4) General procedure: To the mixture of imine (0.3 mmol) and TFA (0.03 mmol) in DCM (1.5 mL) was added indole (0.66 mmol, 2.2 equiv). This reaction mixture was stirred at room temperature in a showed reaction time. Direct purification of reaction mixture by column chromatography on silica gel (petroleum ether/EtOAc: 5/1-3/1) gave the desired product.

Reference： [1]Wang, You-Qing; Wei, Zhong-Shu; Zhu, Chao-Qun; Ren, Yuan-Yuan; Wu, Chunrui [Tetrahedron, 2016, vol. 72, # 31, p. 4643 - 4654]

34
[ 3420-02-8 ]
[ 257-07-8 ]
11-(6-methyl-1H-indol-3-yl)-10,11-dihydrodibenzo[b,f][1,4]oxazepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With trifluoroacetic acid In tetrahydrofuran at 20℃; for 1h;	1 4.2. General procedure for the single aza-Friedele-Crafts reaction in THF (Scheme 3) General procedure: To the mixture of imine (0.3 mmol) and TFA (0.03 mmol) in THF (1.5 mL) was added indole (0.66 mmol). This reaction mixture was stirred at room temperature in a showed reaction time. Direct purification of reaction mixture by column chromatography on silica gel (petroleum ether/EtOAc: 15/1-20/1) gave the desired product.

Reference： [1]Wang, You-Qing; Wei, Zhong-Shu; Zhu, Chao-Qun; Ren, Yuan-Yuan; Wu, Chunrui [Tetrahedron, 2016, vol. 72, # 31, p. 4643 - 4654]

35
[ 3420-02-8 ]
11-(1H-indol-3-yl)-10,11-dihydrodibenzo[b,f][1,4]oxazepine [ No CAS ]
2-(2-((1H-indol-3-yl)(6-methyl-1H-indol-3-yl)methyl)phenoxy)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With trifluoroacetic acid In dichloromethane at 20℃; for 0.5h;	4.4. General procedure for the synthesis of unsymmetric bis-indole compounds (Scheme 6) General procedure: To a mixture of 3aa (0.3 mmol) and TFA (0.03 mmol) in DCM (1.5 mL) was added indole (0.45 mmol). This reaction mixture was stirred at room temperature and monitored by TLC. Upon completion, the reaction mixture was loaded directly atop awet-packed silica gel column. Column chromatography with EtOAc in petroleum ether as eluent afforded the desired product 5.

Reference： [1]Wang, You-Qing; Wei, Zhong-Shu; Zhu, Chao-Qun; Ren, Yuan-Yuan; Wu, Chunrui [Tetrahedron, 2016, vol. 72, # 31, p. 4643 - 4654]

36
[ 3420-02-8 ]
[ 87751-69-7 ]
[ 1431640-79-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(η3-allyl-μ-chloropalladium(II)); N-[2'-(diphenylphosphino)-6'-naphthalenyl]-N-cinnamyladamantanamine; potassium carbonate In acetonitrile at 40℃; for 18h; Inert atmosphere; enantioselective reaction;
54%	With bis(η3-allyl-μ-chloropalladium(II)); potassium acetate; (S)-N-cinnamyl-2-(diphenylphosphanyl)-6-methoxy-N-(1-phenylethyl)aniline In toluene at 40℃; for 18h; Inert atmosphere; enantioselective reaction;	General Procedure for the Palladium-Catalyzed Allylic Alkylation of Indoles. General procedure: To a mixture of indole or substituted indole (0.2 mmol), 1,3-diaryl-2-propenyl acetate(60.6 mg, 0.24 mmol), (S)-6a (6.3 mg, 12 μmol), [Pd(h3-C3H5)Cl]2 (2.2 mg, 6 μmol), andKOAc (39.3 mg, 0.4 mol) was added PhMe (0.2 mL) at room temperature under an Aratmosphere. After stirring for 18 h at 40 °C, the mixture was quenched with water anddiluted with diethyl ether. The organic layer was washed with water and brine, and driedover MgSO4. The filtrate was concentrated with a rotary evaporator and the residue waspurified by column chromatography (elution with n-hexane/EtOAc/Et3N = 20/2/1).

Reference： [1]Mino, Takashi; Nishikawa, Kenji; Asano, Moeko; Shima, Yamato; Ebisawa, Toshibumi; Yoshida, Yasushi; Sakamoto, Masami [Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7509 - 7519]
[2]Mino, Takashi; Yamaguchi, Daiki; Kumada, Manami; Youda, Junpei; Saito, Hironori; Tanaka, Junya; Yoshida, Yasushi; Sakamoto, Masami [Synlett, 2021, vol. 32, # 5, p. 532 - 538]

37
[ 3420-02-8 ]
[ 1596268-38-0 ]
3-[(4-methoxyphenyl)(6-methyl-1H-indol-3-yl)methyl]-1,2-hexadiene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 19h; Schlenk technique; Inert atmosphere; regioselective reaction;
59%	With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 19h; Inert atmosphere;	19 The procedure of Example 1 was followed except that the substrate and reagents used were 1- (4-methoxyphenyl) -2-propyl-2,3-butadiene-1-ol (436.3 mg (19.3 mg, 0.1 mmol) in 10 mL of 1,2-dichloroethane at room temperature for 19 hours to give 3-methyl-indole (392.6 mg, 3 mmol) and tris- (4-methoxyphenyl) -4- (6-methylpindol-3-yl) -1,2-enene (391.8 mg, 59%) (PE / EA = 50: 1): oily liquid; Take a dry reaction tube,Under the nitrogen gas three times.Under nitrogen protection,1- (4-methoxyphenyl) -2-butyl-2,3-butadiene-1-ol (463.4 mg, 2 mmol) was added successively to the reaction tube,And 1,2-dichloroethane (10 mL),A solution of indole (351.7 mg, 3 mmol)And monohydrate p-toluene sulfone (TsOH · H2O, 18.9 mg, 0.1 mmol).The reaction was stirred at room temperature for 18 hours,TLC tracking indicates complete reaction,The reaction solution was filtered through a short silica gel column,Ether leaching,The column was removed by rapid column chromatography (PE (petroleum ether) / EA (ethyl acetate) = 50: 1-30: 1)(4-methoxyphenyl) -4- (1H-indol-3-yl) -1,2-enene

Reference： [1]Guo, Binjie; Huang, Xin; Fu, Chunling; Ma, Shengming [Chemistry - A European Journal, 2016, vol. 22, # 51, p. 18343 - 18348]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN106588749, 2017, A Location in patent: Paragraph 0059; 0146; 0147; 0148; 0149

38
[ 3420-02-8 ]
[ 7677-24-9 ]
6-methyl-2-(6-methyl-1H-indol-3-yl)-3-oxoindoline-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium acetate; silver carbonate In N,N-dimethyl-formamide at 80℃; for 12h; regioselective reaction;	5. General Procedure for the Preparation of 6. General procedure: To a solution of indole (0.3 mmol), Ag2CO3 (0.105 mmol), TMSCN (0.2 mmol), and NaOAc (0.03 mmol) in DMF (1 mL) was added TEMPO (0.045 mmol) under an air atmosphere and the mixture was stirred at 80 °C for 12 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: EtOAc/PE = 1:2) to yield the corresponding product 6.

Reference： [1]Jiang, Lili; Peng, Xiangjun; Huang, Panpan; Chen, Zhengwang; Liu, Liangxian [Tetrahedron, 2017, vol. 73, # 11, p. 1389 - 1396]

39
[ 3420-02-8 ]
[ 75702-97-5 ]
1-cyclopropyl-2,2,2-trifluoro-1-(6-methyl-1H-indol-3-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With caesium carbonate In acetonitrile at 20℃; for 5h;	General procedure for the alkylation of indoles withtrifluoromethyl ketones General procedure: A 4 mL vial was charged with indole or its derivative (1 mmol) and cesium carbonate (0.1 mmol), then 1-cyclopropyl-2,2,2-trifluoroethanone (1 mmol) and MeCN (0.5 mL) was added rapidly. The reaction mixture was stirred at room temperature for appropriate time. The completeness of the reaction was monitored by TLC. When the reaction was completed, the reaction mixture was filtered to remove cesium carbonate and then purified by column chromatography on silica gel to afford the desire product.

Reference： [1]Liu, Xiao-Dong; Wang, Yi; Ma, Hai-Yan; Xing, Chun-Hui; Yuan, Yu; Lu, Long [Tetrahedron, 2017, vol. 73, # 16, p. 2283 - 2289]

40
[ 3420-02-8 ]
[ 100-97-0 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iodine; oxygen; pyrographite; In N,N-dimethyl-formamide; at 120℃; for 0.8h;	General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 molpercent) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2877 - 2880

41
[ 3420-02-8 ]
[ 38896-30-9 ]
methyl 2-(6-methyl-1H-indol-3-yl)quinoline-6-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3390 - 3393

42
[ 107-21-1 ]
[ 108-44-1 ]
[ 3420-02-8 ]
[ 16096-32-5 ]
[ 102-41-0 ]
[ 3477-33-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;	4.1. General procedure General procedure: 1 mmol of amine, 0.07 mmol of Pd/C, 3 mmol of ZnO, 6 mL of distilled water and 6 mL of ethylene glycol were mixed manually inside a 20 mL Teflon flask. Then it was sealed into a steel autoclave and introduced in a preheated oven at 150 °C for 24 h. The reaction mixture was cooled to room temperature, 25 mL of distilled water were added and the crude was filtered through a 0.2 mm Teflon filter. The reaction mixture was extracted with ethyl acetate3 15 ml and organic layers were combined, dried with Na2SO4, filtered and concentrated affording the reaction crude that was cheeked by NMR. Crude reaction was purified by chromatotron (1 mm, silica, from hexane to hexane/AcOEt 1:3) affording pure β-amino alcohols.

Reference： [1]Llabres-Campaner, Pedro J.; Ballesteros-Garrido, Rafael; Ballesteros, Rafael; Abarca, Belén [Tetrahedron, 2017, vol. 73, # 37, p. 5552 - 5561]

43
[ 3420-02-8 ]
[ 1262034-08-1 ]
C₂₃H₂₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium carbonate; platinum(II) chloride In 1,4-dioxane at 100℃; Sealed tube;	5 Synthesis of Compound 5 To an oven-dried flask was added PtCl2 (1.0 g, 0.0038 mol), Na2CO3 (6.1 g, 0.057 mol), 6-methyl indole (10.0 g, 0.076 mol) and compound 2 (10.0 g, 0.038 mol) in dioxane (250 mL). The flask was degassed with nitrogen, sealed and heated to 100° C. overnight. After the reaction was complete (monitored by TLC using 10% ethyl acetate/hexanes). The solvent was evaporated under reduced pressure. The reaction mixture diluted with ethyl acetate (400 mL), reaction mixture was washed with water, saturated NaCl and dried over Na2SO4. The solvent was filtered and concentrated in vacuo to give as brown oil. Crude compound purified by column chromatography (10% ethyl acetate/hexane). Compound 5 was obtained as a light brown solid (6.5 g, 47%).
47%	With sodium carbonate; platinum(II) chloride In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube;	5 Synthesis of compound 5 To an oven-dried flask was added PtC12 (1.0 g, 0.0038 mol), Na2C03 (6.1g, 0.057 mol), 6-methyl indole (10.0 g, 0.076 mol) and compound 2 (10.0 g, 0.038 mol) in dioxane (250 mL). The flask was degassed with nitrogen, sealed and heated to 100°C overnight. After the reaction was complete (monitored by TLC using 10% ethyl acetate/hexanes). The solvent was evaporated under reduced pressure. The reaction mixture diluted with ethyl acetate (400mL), reaction mixture was washed with water, saturated NaCl and dried over Na2SC>4. The solvent was filtered and concentrated in vacuo to give as brown oil. Crude compound purified by column chromatography (10% ethyl acetate/hexane). Compound 5 was obtained as a light brown solid (6.5 g, 47%).

Reference： [1]Current Patent Assignee: VERSICOLOR TECHNOLOGIES LLC - US2017/260133, 2017, A1 Location in patent: Paragraph 0222
[2]Current Patent Assignee: VERSICOLOR TECH; VERSICOLOR TECHNOLOGIES LLC - WO2019/200232, 2019, A1 Location in patent: Paragraph 0794

44
[ 3420-02-8 ]
diisopropyl (1,1‐dioxidobenzo[d]isothiazol‐3‐yl)phosphonate [ No CAS ]
(R)-diisopropyl (3-(6-methyl-1H-indol-3-yl)-1,1-dioxido-2,3-dihydrobenzo[d]isothiazol-3-yl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: diisopropyl (1,1‐dioxidobenzo[d]isothiazol‐3‐yl)phosphonate With (S)-3,3'-bis[3,5-di(trifluoromethyl)phenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid In 1,3,5-trimethyl-benzene at 30℃; for 0.166667h; Schlenk technique; Stage #2: 6-methylindole In 1,3,5-trimethyl-benzene at 30℃; Schlenk technique; enantioselective reaction;	General procedure for the catalytic enantioselective Friedel-Crafts reaction General procedure: Cyclic α-ketiminophosphonates 1 (0.1 mmol) and CPA (S)-4 (5 mol%) were placed in a Schlenk tube and mesitylene (2 mL) was added. The mixture was stirred at 30 °C for 10 min. Then, indoles 2 (0.3 mmol) were added. The resulting mixture was stirred at 30 °C until cyclic α-ketiminophosphonates 1 were completely consumed. The crude product was purified by flash chromatography on silica gel with a mixture of dichloromethane and methanol as the eluent to give chiral quaternary α-aminophosphonates 3.

Reference： [1]Yan, Zhong; Gao, Xiang; Zhou, Yong-Gui [Cuihua Xuebao/Chinese Journal of Catalysis, 2017, vol. 38, # 5, p. 784 - 791]

45
[ 3420-02-8 ]
[ 50-00-0 ]
[ 4771-49-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With iron(III) chloride; ammonia; In water; N,N-dimethyl-formamide; at 130℃; for 1h;	General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37percent aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25percent aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 molpercent), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 °C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane?EtOAc).

Reference： [1]Synlett,2017,vol. 28,p. 2670 - 2674

46
[ 505-18-0 ]
[ 3420-02-8 ]
6-methyl-3-(piperidin-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 2,3,4,5-tetrahydropyridine With methanesulfonic acid In water for 0.166667h; Green chemistry; Stage #2: 6-methylindole With tetra-(n-butyl)ammonium iodide In water at 60℃; for 18h; Green chemistry;	2. General procedure for the Mannich reaction General procedure: To a solution of methanesulfonic acid (0.33 mmol) in water (5 mL) was added imine 1 (0.4 mmol) under vigorous stirring. After stirring for 10 min, TBAI (0.1 mmol) and the corresponding indole (0.33 mmol) were added. The reaction mixture was stirred at 60 °C to complete the transformation (TLC monitoring). After that the reaction mixture was quenched with saturated NaHCO3 (15 mL) and extracted with ethyl acetate (3×15 mL). The combined organic extracts were dried over Na2SO4, concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography silica gel plate to afford target product.

Reference： [1]Xie, Liang-Hui; Cheng, Jie; Luo, Zi-Wei; Lu, Gui [Tetrahedron Letters, 2018, vol. 59, # 5, p. 457 - 461]

47
[ 3420-02-8 ]
[ 431-46-9 ]
C₁₁H₁₀F₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%Chromat.	With triethylamine; In dimethyl sulfoxide; at 80℃; for 0.75h;Microwave irradiation; Green chemistry;	General procedure: Indole (0.35 mmol, 1 eq.), trifluoroacetaldehyde methylhemiacetal (270 μL, 7eq.), triethylamine (7 μL, 10 mol %), and DMSO (0.5 mL) were mixed together in a microwave vial (10 mL). Thesolution was irradiated in the microwave reactor at 80C for 45 min. After cooling to room temperature thereaction mixture was diluted with 2 mL of dichloromethane and washed with water (3x 5 mL). The solvent wasevaporated under vacuum and the crude product was purified by preparative thin layer chromatography.

Reference： [1]Arkivoc,2017,vol. 2018,p. 122 - 130

48
[ 3420-02-8 ]
[ 776-76-1 ]
6-methyl-1-(methyldiphenylsilyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With dodecacarbonyl-triangulo-triruthenium In toluene at 120℃; for 12h; Schlenk technique; Inert atmosphere;	4.2. General procedure for Ru3(CO)12-Catalyzed dehydrogenative Si-N coupling General procedure: Condition A: A mixture of 33 indole (1) (0.2mmol, 1 equiv), hydrosilane (2) (0.3mmol, 1.5 equiv), 16 Ru3(CO)12 (1.9mg, 0.003mmol, 1.5mol %), were weighted in a Schlenk tube equipped with a stir bar. Dry 11 toluene (2.0mL) was added and the mixture was stirred at 120°C for 12h under Ar atmosphere. Afterwards, it was diluted with CH2Cl2 and transferred to a 50mL round bottom flask. Silica was added to the flask and solvents were evaporated under reduced pressure. Flash column chromatography on silica gel with EtOAc:petroleum ether=1:100 as eluent afforded the 47 N-silylated indole.

Reference： [1]Zhai, Wenchao; Li, Bin; Wang, Baiquan [Tetrahedron, 2018, vol. 74, # 11, p. 1123 - 1128]

49
[ 3420-02-8 ]
[ 635-46-1 ]
2-(6-methyl-1H-indol-3-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With oxygen; toluene-4-sulfonic acid; copper(l) chloride In tert-Amyl alcohol at 120℃; for 13h;	9 0.5 mmol of tetrahydroquinoline, 0.5 mmol of 6-methylindole, tetrahydroquinoline 10% copper chloride, tetrahydroquinoline 50% p-toluenesulfonic acid and1.2 ml of tert-amyl alcohol was stirred under an oxygen condition at 120 °C for 13 hours. After the reaction was completed, it was cooled to room temperature, the reaction solution was diluted, filtered, and the filtrate was evaporated. The solvent was evaporated under reduced pressure to give a crude product. Purification by column chromatography gave the product 9a as a yellow oil.
65%	With C₂₅H₂₉ClIrNO In 2,2,2-trifluoroethanol at 50℃; for 16h; Inert atmosphere; Schlenk technique;
	Multi-step reaction with 2 steps 1: tert.-butylhydroperoxide; caesium carbonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / toluene / 16 h / 110 °C / Inert atmosphere; Schlenk technique 2: tert.-butylhydroperoxide; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / toluene / 110 °C / Schlenk technique; Sealed tube

Reference： [1]Current Patent Assignee: WUYI UNIVERSITY - CN109651333, 2019, A Location in patent: Paragraph 0131; 0132; 0134
[2]Chen, Xiuwen; Li, Yibiao; Chen, Lu; Zhu, Zhongzhi; Li, Bin; Huang, Yubing; Zhang, Min [Journal of Organic Chemistry, 2019, vol. 84, # 6, p. 3559 - 3565]
[3]Chen, Xiuwen; Zhao, He; Chen, Chunlian; Jiang, Huanfeng; Zhang, Min [Organic Letters, 2018, vol. 20, # 4, p. 1171 - 1174]

50
[ 3420-02-8 ]
[ 114744-50-2 ]
5-bromo-2-(6-methyl-1H-indol-3-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1171 - 1174

51
[ 3420-02-8 ]
[ 1147550-11-5 ]
[ 1112908-20-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;
98%	With copper(II) choride dihydrate; oxygen In ethanol at 20℃; for 24h; Irradiation;	12 Example 12: The CuCl2·2H2O catalytic system catalyzes the reaction of 6-methylindole and ammonium thiocyanate. Add 6-methylindole (0.2 mmol), NH4SCN (0.6 mmol), CuCl2·2H2O (20 mol%) and ethanol (2 mL) to a dry reaction tube with a magnetic stir bar and place the reaction tube in In the O2 atmosphere,Under the irradiation of a 45 W incandescent lamp, the reaction was stirred at room temperature for 24 h. After the reaction is completed, after the solvent is rotary evaporated,Add 5 mL of saturated brine and extract with 3×5 mL of ethyl acetate. Combine the organic phases. The organic phases are dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated by rotary evaporation and separated by silica gel column chromatography.The target product was obtained (yield 98%). Replace CuCl2·2H2O with copper sulfate pentahydrate,The rest is unchanged, and the product yield is 68%.
97%	With oxygen In tetrahydrofuran at 25℃; for 7h; Irradiation;

Reference： [1]Zhang, Xing; Wang, Chenguang; Jiang, Hong; Sun, Linhao [RSC Advances, 2018, vol. 8, # 39, p. 22042 - 22045]
[2]Current Patent Assignee: SOOCHOW UNIVERSITY (SUZHOU) - CN111205215, 2020, A Location in patent: Paragraph 0062-0065
[3]Chen, Xiong; Feng, Xiao; Han, Songjie; Li, Chunzhi; Li, He; Li, Ziping; Liu, Xiaoming; Shao, Pengpeng; Xia, Hong [Journal of Materials Chemistry A, 2020, vol. 8, # 17, p. 8706 - 8715]

52
[ 3420-02-8 ]
[ 40996-91-6 ]
3-(2-(6-methyl-1H-indol-3-yl)ethyl)cyclohex-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With bismuth(lll) trifluoromethanesulfonate In methanol; acetonitrile at 60℃; for 3h; Sealed tube; regioselective reaction;	5.6 5.4 Representative procedure for the 1,6-addition of electron-rich heteroarenes to 3-vinyl-2-cyclohexenone General procedure: To a 1 dram vial was added Bi(OTf)3 (6.7mg, 0.010mmol, 0.025 equiv), indole (47mg, 0.40mmol), 3-vinyl-2-cyclohexenone (97.7mg, 0.80mmol), and acetonitrile/methanol (10:1) solution (0.8mL). The vial was sealed with a PFTE/silicone-lined septum cap. The reaction was heated to 60°C and allowed to stir at this temperature for 3h. The mixture was cooled and concentrated under reduced pressure. The crude reaction mixture was purified by flash column chromatography on silica gel (hexanes/ethyl acetate=80:20 to 70:30) to yield a white solid (82.1mg, 0.343mmol, 86%).

Reference： [1]Metz, Tanner L.; Leng, Mingwan; Evans, Joshua; Stanley, Levi M. [Tetrahedron, 2018, vol. 74, # 26, p. 3283 - 3292]

53
[ 3420-02-8 ]
[ 1561023-51-5 ]
6-methyl-3-((3-methoxyphenyl)thio)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With oxygen; acetic acid; potassium iodide; sodium nitrite In acetonitrile at 80℃; for 20h; Sealed tube; Green chemistry; regioselective reaction;	3-[(3-Methoxyphenyl)thio]-1H-indole (3aa):Typical Procedure General procedure: A 15 mL tube equipped with a magnetic stirring bar wascharged with 1H-indole (0.5 mmol), sodium S-(3-methoxyphenyl)thiosulfate (0.6 mmol), KI (20 mol%), and NaNO2 (10 mol%).The tube was then sealed with a rubber plug, and MeCN (3 mL)and HOAc (0.5 mL) were injected into the tube. The air in thetube was replaced by charging with oxygen, and the mixturewas stirred under an oxygen atmosphere (balloon) at 80 °Cuntil the reaction was complete (GC). The mixture was cooledto r.t. and the solvent was removed under vacuum. The residuewas washed with 10% aq Na2S2O3 (30 mL) and extracted withCH2Cl2 (4 × 20 mL). The organic layer was then dried (Na2SO4)and concentrated under vacuum. The residue was further purifiedby flash column chromatography (silica gel, PE-Et2O) togive a light-yellow solid; yield: 92 mg (72%); mp 87.6-88.4 °C.
72%	With oxygen; acetic acid; potassium iodide; sodium nitrite In acetonitrile at 80℃; for 20h; Sealed tube;	14 Example 14: Preparation of 6-methyl-3-m-methoxyphenylthio-1H-indole (Formula 6) In a 15 mL glass tube, 3 mL of acetonitrile, 0.5 mmol of 6-methyl-1H-indole, 0.6 mmol of 3-methoxyphenylthiosulfate, 0.1 mmol of KI, and 0.05 mmol of NaNO2 were added. The air in the reaction tube was replaced with oxygen, and the bottle was sealed with a rubber stopper. Then, an oxygen balloon was inserted, and 0.5 mL of HOAc was added to the reaction tube by a syringe. The reaction tube was placed in an oil bath previously heated to 80 ° C, and reacted for 20 hours with stirring. . Distilled under reduced pressure, stirred with sodium thiosulfate solution, and then extracted with dichloromethane. The organic layer was separated, dichloromethane was evaporated under reduced pressure, and then purified by column chromatography to give diethyl ether / petroleum ether volume ratio 1:5 The mixture was used as an eluent, and the eluent containing the target compound was collected, and the solvent was evaporated to give 6-methyl-3-m-methoxyphenylthio-1H-indole. The isolated yield was 72%.

Reference： [1]Xu, Chaorong; Yi, Shanli; Li, Meichao; Hu, Xinquan; Sun, Nan; Jin, Liqun; Hu, Baoxiang; Shen, Zhenlu [Synlett, 2018, vol. 29, # 14, p. 1914 - 1920]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN108586310, 2018, A Location in patent: Paragraph 0052; 0053

54
[ 3420-02-8 ]
(1H-indol-4-yl)(phenyl)methanol [ No CAS ]
3-[(1H-indol-4-yl)(phenyl)methyl]-6-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In 1,2-dichloro-ethane at 70℃; for 15h;	4-[(1H-Indol-3-yl)methyl]-1H-indoles 3; General Procedure General procedure: Catalyst 4a (0.01 mmol), 4-indolylmethanol 1 (0.1 mmol) and 1H-in-dole (2; 0.4 mmol) were mixed in 1,2-dichloroethane (0.5 mL) in a dried tube. Then, the mixture was stirred at 70 °C for 15 h. After thecompletion of the reaction which was determined by TLC, the mix-ture was concentrated in vacuo. The residue was purified throughpreparative TLC to afford pure products 3.

Reference： [1]Liu, Jin-Xi; Zhu, Zi-Qi; Yu, Lei; Du, Bai-Xiang; Mei, Guang-Jian; Shi, Feng [Synthesis, 2018, vol. 50, # 17, p. 3436 - 3444]

55
[ 3420-02-8 ]
[ 121-69-7 ]
[ 75-05-8 ]
N,N-dimethyl-4-((6-methyl-1H-indol-3-yl)methyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dipotassium peroxodisulfate In water at 20℃; for 2h;	(15) General procedure for the synthesis of 3-arylmethylindoles 3: General procedure: A mixture of N,N-dimethylaniline 1 (2.0 mmol), indole 2 (1.0mmol), K2S2O8 (1.5 equiv), and CH3CN (3 mL) was taken in aflask and stirred at r.t. for 2-4 h (Scheme 2). After completion ofthe reaction (monitored by TLC), water (5 mL) was added andthe mixture was extracted with ethyl acetate (3 × 5 mL). Thecombined organic phase was dried over anhydrous Na2SO4, filtered,and evaporated under reduced pressure. The resultingcrude product was purified by silica gel chromatography using amixture of hexane/ethyl acetate (4:1) as eluent to afford an analyticallypure sample of product 3.

Reference： [1]Singh, Manjula; Yadav, Arvind K.; Yadav, Lal Dhar S.; Singh, Rana Krishna Pal [Synlett, 2018, vol. 29, # 17, p. 2306 - 2310]

56
[ 3420-02-8 ]
[ 824-79-3 ]
3-iodo-6-methyl-2-tosyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tert.-butylhydroperoxide; iodine In ethanol at 80℃; for 12h;	5.2 5.1.5 Synthesis of compounds 5a-e General procedure: To a solution of 1H-indoles 1a-c (1.0mmol), sodium aryl sulfonates 4a, 4e and 4h (0.5mmol, 1.0 equiv), catalyst I2 (1.5mmol) and tert-Butyl hydroperoxide (1.5mmol) in C2H5OH (2mL) were added. The reaction mixture was stirred at 80°C for 12h. Then the reaction mixture was cooled to room temperature, diluted with brine (15mL) and extracted with EtOAc (3×25mL). The organic layer dried over anhydrous MgSO4 and concentrated in vacuo. The pure products 5a-e was obtained by column chromatography on silica gel (Petroleum ether/EtOAc=5:1) with yield of 31%-65%.

Reference： [1]Xia, Qinqin; Bao, Xiaodong; Sun, Chuchu; Wu, Di; Rong, Xiaona; Liu, Zhiguo; Gu, Yugui; Zhou, Jianmin; Liang, Guang [European Journal of Medicinal Chemistry, 2018, vol. 160, p. 120 - 132]

57
[ 3420-02-8 ]
[ 591-50-4 ]
benzene-1,3,5-triyl triformate [ No CAS ]
3,3'-(phenylmethylene)bis(6-methyl-1H-indole) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With bis-triphenylphosphine-palladium(II) chloride; formic acid; triethylamine; tris-(o-tolyl)phosphine In dimethyl sulfoxide at 70℃; for 24h;	1. Typical reaction procedure General procedure: PdCl2(PPh3)2 (0.1 mmol), P(o-tolyl)3 (0.1 mmol), TFben(0.5 mmol) and indole (1.0 mmol) were transferred into an ovendriedtube (15 mL), which was evacuated and backfilled withN2(5x). DMSO (2 mL), aryl iodide (1.2 mmol), Et3N (1 mmol) andHCO2H (1.5 mmol) were added into the tube via syringe. The reactionmixture was stirred at 70 °C for 24 h. After the reaction wascomplete, the mixture was filtrated and extracted with DCM. Thecombined organic layers were washed with H2O and brine, driedover anhydrous Na2SO4, and then concentrated under vacuum.The crude product was purified by column chromatography on silicagel (petroleum ether/ethyl acetate = 20/1) to afford the product.

Reference： [1]Qi, Xinxin; Ai, Han-Jun; Zhang, Ning; Peng, Jin-Bao; Ying, Jun; Wu, Xiao-Feng [Journal of Catalysis, 2018, vol. 362, p. 74 - 77]

58
[ 3420-02-8 ]
[ 24415-66-5 ]
5-methyl-7-(6-methyl-1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide; at 100℃; for 6h;Sealed tube;	The preparation method of the compound e30 comprises the steps of: taking about 1 mmol of <strong>[24415-66-5]7-chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine</strong> and about 3 mmol.6-Methyl-1H-indole was added to a 10 mL microwave reaction tube.Further, 2 mL of hexafluoroisopropanol solvent and about 0.1 mmol of bistrifluoromethanesulfonimide catalyst were added, sealed and heated to 100 C with stirring and reacted for about 6 h.Then, the reaction system was monitored by TLC, and after the reaction system was cooled to room temperature, it was separated and purified by column chromatography to obtain pure compound e30.The compound e30 is a yellow solid with a yield of 63%.
63%	With 1,1,1,3',3',3'-hexafluoro-propanol; bis(trifluoromethanesulfonyl)amide; at 100℃; for 6h;Microwave irradiation; Sealed tube;	Adding 85 mg (about 0.5 mmol) to a 10 mL microwave reaction tube.<strong>[24415-66-5]7-Chloro-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine</strong> and 197 mg (about 1.5 mmol) of 6-methylindole, 14 mg (about 10 mol%) of catalyst Bis-trifluoromethylsulfonimide and 1 mL of solvent HFIP, and then sealed the microwave reaction tube.Then, the reactant in the microwave reaction tube was stirred at 100 C for 6 hours, and the solvent was distilled off under reduced pressure.And purified by column chromatography using DCM / MeOH as eluent to give about 84 mg of pure product e8 as a yellow solid, yield 63%;

Reference： [1]Patent: CN109020976,2018,A .Location in patent: Paragraph 0183; 0184; 0185; 0186
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 59 - 66
[3]Patent: CN109180684,2019,A .Location in patent: Paragraph 0051; 0052; 0053; 0054

59
[ 3420-02-8 ]
[ 3876-05-9 ]
3-chloro-4-(6-methyl-1H-indol-3-yl)-1-phenyl-1H-pyrrole-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.8%	Stage #1: 6-methylindole With ethylmagnesium bromide In diethyl ether; benzene at 20℃; for 0.5h; Stage #2: 3,4-dichloro-1-phenyl-1H-pyrrole-2,5-dione In tetrahydrofuran; diethyl ether; benzene at 20℃; for 4h;	2 4.1.1. 3-Chloro-4-(6-methoxy-1H-indol-3-yl)-1-phenyl-1H-pyrrole-2,5-dione (2c) General procedure: To a solution of indole 1c (5.7g, 39.0mmol) in dry benzene (10mL), EtMgBr (5.0g, 37.5mmol) in dry Et2O (15mL) was added dropwise at room temperature. After stirring for 30min, the resuted mixture was added dropwise to a solution of 3,4-dichloro-1-phenyl-1H-pyrrole-2,5-dione (6.1g, 25mmol) in dry THF (10mL) at room temperature. The resulted mixture was then stirred for 4h. After that, it was adjusted to weak acidity with 1M aqueous hydrochloric acid and extracted with ethyl acetate (3×100mL). The organic phase was combined and washed with brine (3×300mL), dried over Na2SO4 and concentrated in vacuo. The residue was recrystallized from ethyl acetate to get 5.6g (64.0%) 2c as a red solid.
	With ethylmagnesium bromide In tetrahydrofuran

Reference： [1]Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia [Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 4, p. 589 - 603]
[2]Xu, Jianghong; Hu, Yuanyuan; Liu, Xiaoqi; Gao, Anhui; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Hu, Chunqi; Li, Ji [Pharmaceutical Chemistry Journal, 2021, vol. 55, # 7, p. 655 - 664]

60
[ 3420-02-8 ]
[ 3419-91-8 ]
6'-methyl-1-(pyridin-2-yl)-1H,1'H-2,2'-biindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With silver hexafluoroantimonate; carbonyl(η-5-cyclopentadienyl)diiodocobalt(III); sodium acetate; silver(l) oxide; Trimethylacetic acid In toluene at 110℃; for 11h; Inert atmosphere;	2.1; 2.2 (1) 0.2 mmol of the N-pyridyl ruthenium compound under an empty atmosphere6-methyl indole 0.45 mmol,[Cp*Co(CO)I2] 0.006mol,AgSbF60.02mmol,HOPiv 0.05mmol,Ag2O 0.4mmol,0.22 mmol of NaOAc and 3 ml of toluene were mixed in a reaction tube.Heating in a 110 ° C oil bath for 11 h;
72%	With silver hexafluoroantimonate; [Cp*Co(CO)I₂]; sodium acetate; silver(l) oxide; Trimethylacetic acid In 1,2-dichloro-ethane at 110℃; for 12h; regioselective reaction;

Reference： [1]Current Patent Assignee: NANYANG NORMAL UNIVERSITY - CN109305960, 2019, A Location in patent: Paragraph 0044; 0046; 0047; 0048; 0049; 0050
[2]Li, Ting; Yang, Yuhan; Li, Bo; Yang, Ping [Chemical Communications, 2019, vol. 55, # 3, p. 353 - 356]

61
[ 3420-02-8 ]
[ 137-26-8 ]
6-methyl-1H-indol-1-yl dimethylcarbamodithioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 20℃; for 1h;	General procedure for the synthesis of products 3 General procedure: A mixtureof indole 1 (0.2 mmol), bis(dialkylaminethiocarbonyl)disulfide 2(0.22 mmol), t-BuOK (0.4 mmol), and DCE (2 mL) were added in a5mL glass tube, which was stirred at room temperature for 1e4h.When the reaction was completed, it was mixed with water andethyl acetate. The reaction mixture was extracted three times withethyl acetate. The combined organic layer was dried over anhydrousmagnesium sulfate and filtered. The filtrate was evaporatedunder vacuum and the residue was purified by flash columnchromatography on silica gel (eluted with petroleum ether-ethylacetate) to provide the desired products 3.
96%	With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 25℃; for 1h;	8 Example 8 6-methylindole (0.2 mmol), N, N, N', N'-tetramethyl thiuram (0.22 mmol) were added to a 5 mL reaction flask.Potassium tert-butoxide (0.4 mmol) and DCE (2.0 mL) were stirred at room temperature. TLC tracks the detection reaction. After 1 hour, the reaction was stopped.Water and ethyl acetate were added to the reaction mixture, the organic layer was separated, and then aqueous layer was washed three times with ethyl acetate.Combine all the organic layers, dry over anhydrous sodium sulfate, concentrate, and then chromatograph (17% ethyl acetate petroleum ether)The product was obtained in 48.7 mg, yield 96%.

Reference： [1]Song, Zengqiang; Zhou, Yan; Zhang, Wenxin; Zhan, Lingling; Yu, Yuanzu; Chen, Yuehui; Jia, Wenjing; Liu, Zhiguo; Qian, Jianchang; Zhang, Yali; Li, Chenglong; Liang, Guang [European Journal of Medicinal Chemistry, 2019, vol. 171, p. 54 - 65]
[2]Current Patent Assignee: WENZHOU MEDICAL UNIVERSITY - CN109384702, 2019, A Location in patent: Paragraph 0066-0068

62
[ 3420-02-8 ]
[ 3476-89-9 ]
2-(6-methyl-1H-indol-3-yl)quinoxaline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 3559 - 3565

63
[ 3420-02-8 ]
[ 120-92-3 ]
1-cyclopentyl-6-methylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With 10 mol% Pd(OH)2/C; potassium formate In water at 100℃; for 24h; Inert atmosphere;
71%	With 10% palladium hydroxide on charcoal; potassium formate In water at 100℃; for 24h; Inert atmosphere;	6 In the reaction tube (20 ml) put in moderate and solder, adding palladium hydroxide/carbon (10 µM %), potassium formate (2.5 times equivalent), subsequently the reaction tube vacuum pumping, orifice, repeatedly replacing three times, in the argon atmosphere water (0.5 ml), cyclopentanone (3.0 times equivalent), 6 - methyl indole (0.2 mmol) slowly adding the reaction tube injector, the reaction tube is arranged in the 100 degree Celsius in oil bath heating and stirring the reaction. 24 Hours after stopping the reaction, the reaction tube from out in oil bath, natural cooling to room temperature, methylene chloride (15 ml) to extract respectively 3 times, the combined organic phase, saturated salt water for washing, drying with anhydrous sodium sulfate, filtered, after concentrating the filtrate by column chromatography (eluent: petroleum ether/ethyl acetate=100/1) to obtain the final product 3 f, yield 71%.

Reference： [1]Wang, Zemin; Zeng, Huiying; Li, Chao-Jun [Organic Letters, 2019, vol. 21, # 7, p. 2302 - 2306]
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN109879788, 2019, A Location in patent: Paragraph 0028

64
[ 3420-02-8 ]
[ 2292-60-6 ]
3-(1-(4-methoxyphenyl)isochroman-1-yl)-6-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 3,4-dihydro-1-(4-methoxyphenyl)-1H-2-benzopyran With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 0.5h; Stage #2: 6-methylindole In dichloromethane at 20℃; for 3h;	General procedure for the CDC reaction of α-substituted isochromans 1 with indoles and pyrroles General procedure: To a solution of isochroman 1a (0.1 mmol, 1.0 equiv) in CH2Cl2 (1.0 mL) was added DDQ (0.12 mmol, 1.2 equiv) at rt. The mixture was stirred at that temperature for 0.5 h. After that, indole or pyrrole (0.15 mmol, 1.5 equiv) was added, and the mixture was stirred for another 3 h. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel using CH2Cl2 as an eluent to give the desired product.

Reference： [1]Cao, Min; Mao, Ying; Huang, Jiancheng; Ma, Yudao; Liu, Lei [Tetrahedron Letters, 2019, vol. 60, # 15, p. 1075 - 1078]

65
[ 3420-02-8 ]
C₁₇H₂₁NO₆ [ No CAS ]
C₃₁H₂₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper diacetate In acetonitrile at 80℃; Inert atmosphere;	4 Example 4 The acetophenone oxime acetate substituted with 6-methylindole and diethyl malonate is used as a raw material, and the molar ratio of 6-methyl hydrazine: hydrazine acetate: copper acetate is 1.6:1:2.0.2 mmol of hydrazine acetate, 4 mL of solvent acetonitrile, heated to 80 ° C under N2 protection conditions,The reaction was carried out by TLC, and after all the raw materials were completely reacted, ethyl acetate and water were extracted, dried and dried.After dissolving with ethyl acetate, dichloromethane was washed to give the pure product 3ad, yield 83%.
83%	With copper diacetate In acetonitrile at 80℃; for 1h; Inert atmosphere;

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN109535140, 2019, A Location in patent: Paragraph 0063; 0064; 0065; 0066
[2]Mao, Peng-Fei; Zhou, Li-Jin; Zheng, An-Qi; Miao, Chun-Bao; Yang, Hai-Tao [Organic Letters, 2019, vol. 21, # 9, p. 3153 - 3157]

66
[ 3420-02-8 ]
[ 6904-16-1 ]
2-[2-(6-methyl-1H-indol-3-yl)but-3-en-1-yl]malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; toluene-4-sulfonic acid In acetonitrile at 50℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	Reaction of Vinylcyclopropanes with Indoles; General Procedure General procedure: Under an argon atmosphere, indole 2 (0.1 mmol) and iridium complex(6.7 mg, 0.01 mmol) were added to a dry Schlenk tube. Then, asolution of vinylcyclopropane 1 (0.2 mmol) and p-toluenesulfonic acid (2 mg, 0.01 mmol) in MeCN (1 mL) was added to the reactionmixture, which was stirred at 50 °C for 12 h. After the completion ofthe reaction (TLC monitoring), the mixture was purified by preparativeTLC (eluent for all products: PE/EtOAc, 3:1) to afford the respectivepure product 3.

Reference： [1]Yu, Lei; Zhu, Zi-Qi; Sun, Meng; Mei, Guang-Jian; Shi, Feng [Synthesis, 2019, vol. 51, # 7, p. 1655 - 1661]

67
[ 3420-02-8 ]
[ 87751-69-7 ]
(S)-(-)-3-[(E)-1,3-diphenyl-2-propen-1-yl]-6-methyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis(η3-allyl-μ-chloropalladium(II)); (S)-2′-(tert-butyl)-7-(diphenylphosphino)-2,3-dihydro-5′H-spiro[indene-1,4′-oxazole]; caesium carbonate In toluene at 25℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction;	3.2. General Procedure for the Pd-Catalyzed Asymmetric Allylic Alkylation of Indoles General procedure: Ligand L1 (5.0 mg, 4 mol%) and [Pd(C3H5)Cl]2 (2.2 mg, 2 mol%) were dissolved in toluene(1.0 mL) in a Schlenk tube under Ar. After 0.5 h of stirring at room temperature, allylic acetate 2(0.36 mmol) dissolved in toluene (0.5 mL) was added, followed by indole 1 (0.3 mmol), and Cs2CO3(195 mg, 0.6 mmol). The mixture was stirred at room temperature for 12 h and then was diluted with CH2Cl2 and washed with saturated NH4Cl (aq). The organic layers were dried over MgSO4 and filtered, and the solvents were evaporated in vacuo. The residue was purified by flash column chromatography, eluting with petroleum ether and ethyl acetate to afford the corresponding product 3.

Reference： [1]Qiu, Zhongxuan; Sun, Rui; Yang, Kun; Teng, Dawei [Molecules, 2019, vol. 24, # 8]

68
[ 3420-02-8 ]
2-benzylidene-N-tosylbenzofuran-3(2H)-imine [ No CAS ]
(+)-4-methyl-N-(2-((6-methyl-1H-indol-3-yl)(phenyl)methyl)benzofuran-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In 1,3,5-trimethyl-benzene at -20℃; enantioselective reaction;	General procedure for catalytic enantioselective conjugate addition (+)-4-Methyl-N-(2-((6-methyl-1H-indol-3-yl)(phenyl)methyl)benzofuran-3-yl)benzenesulfonamide (3ag): 91 mg, 90% yield, white solid, m.p. = 231-233 °C, new compound, Rf = 0.10 (hexanes/ethyl acetate = 5:1), 93% ee, [α]20D = +103.80 (c 0.92, EtOAc). 1 H NMR (400 MHz, CDCl3) δ 7.88 (s, 1H), 7.58 (d, J = 8.3 Hz, 2H), 7.34-7.28 (m, 2H), 7.23-7.16 (m, 4H), 7.14-7.05 (m, 5H), 7.02 (d, J = 8.1 Hz, 2H), 6.82 (d, J = 7.3 Hz, 1H), 6.72 (d, J = 1.8 Hz, 1H), 6.05 (s, 1H), 5.59 (s, 1H), 2.41 (s, 3H), 2.22 (s, 3H);13C NMR (100 MHz, CDCl3) δ 155.6, 153.4, 144.1, 140.2, 136.9, 136.4, 132.4, 129.7, 128.6, 128.5, 127.7, 126.9, 126.2, 124.4, 123.2, 122.9, 121.7, 119.7, 119.2, 115.2, 113.2, 111.7, 111.3, 39.9, 21.8, 21.6. HPLC: Chiralcel AD-H column, 254 nm, 30 °C, n-hexane/i-PrOH = 60/40, flow = 0.8 mL/min, retention time 19.3 min and 21.2 min (major). HRMS calculated for C31H26KN2O3S [M+K]+ 542.1296, found: 542.1293.
90%	With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In 1,3,5-trimethyl-benzene at -20℃;	20 General procedure: Add azadiene, chiral phosphoric acid A1 and mesitylene into the reaction flask, put it in a cold bath at -20°C, then add indole, stir and react for 48-72h, direct column chromatography (volume ratio of eluent petroleum ether and ethyl acetate is 5:1) to obtain the corresponding chiral heterotriarylmethane compound; the molar ratio of the azadiene, asymmetrically added indole and the catalyst is 1:1.0:0.05. The yield is the isolated yield, and the enantiomeric excess of the product is determined by chiral liquid chromatography.

Reference： [1]Xie, Huan-Ping; Wu, Bo; Wang, Xin-Wei; Zhou, Yong-Gui [Cuihua Xuebao/Chinese Journal of Catalysis, 2019, vol. 40, # 10, p. 1566 - 1575]
[2]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN111662274, 2020, A Location in patent: Paragraph 0040-0043; 0045; 0066

69
[ 3420-02-8 ]
[ 50845-77-7 ]
(S)-Ethyl 2-(4-Methoxyphenylamino)-2-(6-methyl-1H-indol-3-yl)-acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With rose bengal In acetonitrile at 20℃; for 12h; Irradiation;	7 Example 7 Add 1a (0.209g, 1.0mmol), indole 2d (0.131g, 1.0mmol), Rosebengal (0.010g), and 10mL CH3CN to a 25mL colorimetric tube, and stir under room temperature air. The reaction was irradiated under 34W blue LED for 12 hours. After the reaction, the reaction solution was subjected to column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 0.242 g of 3ad. Indole glycine derivative 3ad: 72% yield;

Reference： [1]Current Patent Assignee: JIANGSU UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN110452151, 2019, A Location in patent: Paragraph 0072-0075

70
[ 3420-02-8 ]
[ 59908-51-9 ]
C₁₇H₁₃ClN₂ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2020,vol. 68,p. 2306 - 2315

71
[ 3420-02-8 ]
[ 97-74-5 ]
N,N,6-trimethyl-1H-indole-1-carbothioamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate In dimethylsulfoxide-d6 at 100℃; for 2h; Sealed tube;	Reaction of 1H-Indoles with Tetramethylthiuram Monosulfide (TMTM); General Procedure General procedure: 1H-Indole (0.5 mmol), TMTM (0.6 mmol), Cs2CO3 (1.0 mmol) and DMSO (2.0 mL) were mixed in a sealed tube and stirred at 100 °C for 2h. The reaction was checked by TLC until the starting material was consumed. The reaction was terminated with sat. NH4Cl solution (4mL) and then extracted with EtOAc. The crude solution was dried overanhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product 3.

Reference： [1]Dong, Zhi-Bing; Peng, Han-Ying; Wu, Yu-Xi [Synthesis, 2020, vol. 52, # 1, p. 135 - 140]

72
[ 3420-02-8 ]
[ 36635-61-7 ]
6-methyl-3-(tosylmethyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With ferrous(II) sulfate heptahydrate In water at 110℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	General Procedure for Preparation of Products 3 and 4 General procedure: To a 15 mL two-necked Schlenk tube fitted with glass stopper were added indoles 1 (0.1 mmol),TosMIC derivatives 2 (0.3 mmol), and FeSO4·7H2O (0.015 mmol, 4.2 mg) in a mixed solvent of H2O and PEG400 (v/v = 3/2, 2 mL) under an Ar atmosphere using the standard Schlenk techniques. The Schlenk tube was capped and heated at 110 °C for 24 h. The reaction mixture was then cooled toroom temperature and concentrated directly. After removal of solvent, the residue was purified by preparative thin-layer chromatography (petroleum ether/EtOAc = 1:1) to give the desiredproduct 3 and 4.

Reference： [1]Cui, Tian-Wei; Hao, Xin-Qi; Lu, Shuai; Song, Mao-Ping; Yan, Ke-Xin; Zhu, Xinju; Zhu, Yu-Shen [Synlett, 2019, vol. 30, # 16, p. 1924 - 1928]

73
[ 3420-02-8 ]
C₁₈H₁₇NO₃ [ No CAS ]
3-[bis(6-methyl-1H-indol-3-yl)methyl]-1-(4-methoxybenzyl)quinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tert-Butyl peroxybenzoate; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 90℃;	Compounds 3; General Procedure General procedure: To a mixture of indole (1.25 mmol), amide 1 (0.50 mmol), TFA (4.00 mmol), and t-BuOOBz (0.60 mmol) in DMF/DMSO (3 mL, 9:1) was added Pd(OAc)2 (11 mg, 0.05 mmol). The mixture was heated at 90 °C with stirring until compound 1 was consumed (TLC monitoring, 16-36 h). The reaction mixture was cooled to r.t. and diluted with H2O. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with H2O, brine, dried (Na2SO4), and evaporated under reduced pressure. Purification of the crude product by flash column chromatography (PE/acetone 6:1-2:1) provided the desired product 3.

Reference： [1]Duan, Lian; Liu, Sheng; Liu, Yuan-Cui; Qiu, Wen-Zhuang; Wang, Li-Ping; Xie, Kai-Qiang; Zuo, Ming-Xing [Synthesis, 2020, vol. 52, # 11, p. 1680 - 1686]

74
[ 3420-02-8 ]
[ 948-65-2 ]
2-(6-methyl-1H-indol-3-yl)-2-phenylindolin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With C₉H₁₈NO⁽¹⁺⁾*BH₄^(1-) In tetrahydrofuran at 0℃;	General procedure B: General procedure: To a solution of 1 (0.1 mmol) and 4 (0.2 mmol) in THF (1.0 mL) was addedTEMPO+BF4- (0.1 mmol) at 0 °C. The mixture was further stirred until the disappearance of startingmaterial 1 by TLC analysis at 0 °C. The solvent was removed and the residue was purified by flashchromatography using acetone-petroleum ether as eluent to aord the desired product.

Reference： [1]Jiang, Cheng-Shi; Liu, Xigong; Tang, Ying-De; Yan, Xue; Zhang, Hua [Molecules, 2020, vol. 25, # 2]

75
[ 3420-02-8 ]
6,6',6”-trimethyl-[3,2':2',3”-terindolin]-3'-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With C₉H₁₈NO⁽¹⁺⁾*BH₄^(1-) In tetrahydrofuran at 20℃; for 6h;	General procedure D: General procedure: To a solution of C2-substituted indole (0.2 mmol) or indole (0.3 mmol) inTHF (1.0 mL) was added TEMPO+BF4- (0.1 mmol). The mixture was stirred at room temperature for 6 h. The solvent was removed and the residue was purified by flash chromatography usingacetone-petroleum ether as eluent to aord the desired product.

Reference： [1]Jiang, Cheng-Shi; Liu, Xigong; Tang, Ying-De; Yan, Xue; Zhang, Hua [Molecules, 2020, vol. 25, # 2]

76
[ 3420-02-8 ]
[ 286-20-4 ]
2-(6-methyl-3-indoleselenyl)-1-cyclohexyl alcohol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With selenium; tetra-(n-butyl)ammonium iodide; lithium tert-butoxide In water at 20 - 45℃; for 12.0833h; Schlenk technique; Inert atmosphere;	4 Synthesis of 2-(6-methyl-3-indoleselenyl)-1-cyclohexyl alcohol: At room temperature, add a stir bar, selenium powder (0.8mmol), lithium tert-butoxide (1.2mmol), tetrabutylammonium iodide (0.8mmol), 6-methyl-indole (0.4mmol) into a 25mL Schlenk tube , Then evacuated, filled with nitrogen, evacuated back and forth-filled with nitrogen three times, added cyclohexene oxide (0.8mmol) and deionized water (2mL) under the protection of nitrogen, then stirred at room temperature for 5min, and finally moved to 45 The reaction in the heating tank was followed by TLC (or GC-MS) tracking detection during the reaction. After detection, the reaction was completed after 12 hours. After the reaction was completed and the reaction mixture was cooled, the reaction mixture was first diluted with 15 mL of water, and then extracted three times with 45 mL of ethyl acetate. The organic phase was collected three times, and then the organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. PE/EA=4:1 was purified by column to obtain the product. The product was a yellow oily liquid with a yield of 83%.

Reference： [1]Current Patent Assignee: WENZHOU UNIV CANGNAN INSTITUTE - CN108047118, 2021, B Location in patent: Paragraph 0053-0062

77
[ 3420-02-8 ]
[ 2926-29-6 ]
6-methyl-3-((trifluoromethyl)thio)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; 1-hexyl-3-methyl-1-imidazolium bromide In water at 60℃; for 5h; Ionic liquid; chemoselective reaction;	General procedures for the trifluoromethylthiolation of indole and its derivatives General procedure: A mixture of indole (or its derivatives) 1 0.25 mmol, CF3SO2Na 2 0.30 mmol and [Hmim]Br 0.5 mL was charged in an oven-dried reaction vessel, and then concentrated HCl (37 wt.% aqueous solution, 0.5 mmol) was added followed by heating the mixture at 60 oC and stirring for 5 h. Upon completion, the reaction mixture was diluted with MTBE (4.0 mL), filtered through a bed of silica gel layered over Celite. The volatiles were removed in vacuo to afford the crude product. Further column chromatography on silica gel (EtOAc/petroleum ether) was needed to afford the pure desired products 3.

Reference： [1]Wang, Fei; Lu, Guo-Ping; Lin, Yamei [Tetrahedron Letters, 2021, vol. 70]

78
[ 75-07-0 ]
[ 108-44-1 ]
[ 3420-02-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With C₁₄H₂₂B₁₀Br₂FeN₂ In toluene at 20℃; for 2h;	7 The ferrous complex prepared in Example 1 was used as a catalyst to catalyze the synthesis of indole derivatives: Toluene (toluene) solution of ferrous complex (0.004mmol) was added to 3-methylaniline (1mmol), acetaldehyde (1mmol) was added, and the reaction was carried out at room temperature for 120 minutes. After completion, the concentrated reaction solution was directly passed through a silica gel column. Chromatographic separation, drying to the same quality, the corresponding indole derivative C9H9N (yield 91%)

Reference： [1]Current Patent Assignee: SHANGHAI INSTITUE OF TECHNOLOGY - CN113185444, 2021, A Location in patent: Paragraph 0053-0056

79
[ 3420-02-8 ]
[ 2150-46-1 ]
methyl 2-hydroxy-8-methyl-6H-benzofuro[2,3-b]indole-1-carboxylate [ No CAS ]

Reference： [1]Green Chemistry,2021,vol. 23,p. 5031 - 5036

80
[ 3420-02-8 ]
[ 120-46-7 ]
2-(6-methyl-3-oxoindolin-2-ylidene)-1,3-diphenylpropane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium fluoride; di-tert-butyl peroxide; oxygen In toluene at 100℃; for 3h;	General Procedure for preparing diphenylurea derivatives 3 General procedure: Indole (1.0 mmol), 2,4-pentanedione (1.0 mmol), KF (1 mmol), DTBP (2 mmol) and methylbenzene (20 mL) were charged into a 25 mL round-bottom flask, and the mixture was refluxed. The resulting solution was stirred for 3 h until the indole were not consumed. The mixture was cooled to room temperature, then EtOAc (50 mL × 2) was added. The organic phase was washed with water (20 mL), dried over Na2SO4, concentrated and purified by flash column chromatography to afford 3-(3-oxoindolin-2-ylidene)pentane-2,4-dione in a 74% yield.

Reference： [1]Tan, Xiangyu; Zhang, Jianqiang; Liu, Xingyuan; Jin, Yi [Tetrahedron Letters, 2021, vol. 80]

81
[ 3420-02-8 ]
[ 123-54-6 ]
3-(6-methyl-3-oxoindolin-2-ylidene)pentane-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium fluoride; di-tert-butyl peroxide; oxygen In toluene at 100℃; for 3h;	General Procedure for preparing diphenylurea derivatives 3 General procedure: Indole (1.0 mmol), 2,4-pentanedione (1.0 mmol), KF (1 mmol), DTBP (2 mmol) and methylbenzene (20 mL) were charged into a 25 mL round-bottom flask, and the mixture was refluxed. The resulting solution was stirred for 3 h until the indole were not consumed. The mixture was cooled to room temperature, then EtOAc (50 mL × 2) was added. The organic phase was washed with water (20 mL), dried over Na2SO4, concentrated and purified by flash column chromatography to afford 3-(3-oxoindolin-2-ylidene)pentane-2,4-dione in a 74% yield.

Reference： [1]Tan, Xiangyu; Zhang, Jianqiang; Liu, Xingyuan; Jin, Yi [Tetrahedron Letters, 2021, vol. 80]

82
[ 3420-02-8 ]
[ 353-83-3 ]
6-methyl-3-((2,2,2-trifluoroethyl)thio)-1H- indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium dithionite; triphenylphosphine In water; dimethyl sulfoxide at 90℃; for 5h; Schlenk technique;	Synthesis of fluoroethylthiolated indoles General procedure: indoles( 5 mmol) 1a , Na2S2O4 1.5 mmol ), additives and 2 ml solvent were added to a Schlenk sealed tube , following iodofluoroethane 2 (1.5 mmol) was added to the mixture solution and then the resulting mixture was string for 10 mins. After addition , the mixture was allowed for string 12h under set temperature. Then, 10ml water was added, and the reaction mixture was extracted by Ethyl acetate 3 times. The organic layer was combined, washed with brine for once and dried over Na2SO4 . The solvent was removed by reduce pressure rotary evaporation and purified by column chromatography on silica gel with Petroleum ether/ Ethyl acetate to give 3/ 4/ 5 .

Reference： [1]Leng, Faqiang; Huang, Jianjian; Yu, Nianhua; Wang, Guizhao [Tetrahedron Letters, 2021, vol. 85]

83
[ 3420-02-8 ]
[ 1422984-99-3 ]
C₁₈H₁₅F₃N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 6-methylindole With nickel(II) perchlorate hexahydrate; C₅₃H₄₂N₂O₂ In toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: (E)-(3,3,3-trifluoro-1-nitroprop-1-en-2-yl)benzene In toluene at 85℃; for 36h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	3.2 Asymmetric synthesis of indole derivatives containing a trifluoromethylated all-carbon quaternary center though 1,4-addition reactions General procedure: In an argon-filled glovebox, Ni(ClO4)2.6H2O (4.0 mg, 0.011 mmol, 11 mol%), L1 (7.4 mg, 0.01 mmol, 10 mol% ), and indole or substituted indole (0.15 mmol, 1.5 equiv.) were added to a Schlenk tube equipped with a magnetic stir bar. After the reaction tube was sealed with a rubber stopper, it was removed from the glove box and the newly distilled anhydrous toluene (1.0 mL) was added to the tube with a syringe. The reaction was stirred at room temperature for 1 hour and then the disubstituted nitroalkene (0.1 mmol, 1.0 equiv.) was added to the tube carefully with a microinjector. Subsequently, the Schlenk tube was placed into an oil bath which was pre-heated to 85 °C or 100 °C. In order to reduce the volatilization of the toluene, the upper part of the Schlenk tube was cooled by air flow from an electric fan. When the reaction was complete, the solvent was concentrated in vacuo and the residue was subjected to flash silica gel column chromatography (PE/EA = 10:1- 5:1) to afford the product. The enantiomeric excesses were determined by HPLC analysis using chiral stationary phases.

Reference： [1]Bao, Robert Li-Yuan; Shi, Lei; Fu, Kang [Chinese Chemical Letters, 2022, vol. 33, # 5, p. 2415 - 2419]

84
[ 3420-02-8 ]
N-(2-(ethylthio)phenyl)but-3-enamide [ No CAS ]
N-(2-(ethylthio)phenyl)-4,4-bis(6-methyl-1H-indol-3-yl)butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron(III) chloride; palladium diacetate; iron(II) acetate; benzoic acid In acetonitrile at 90℃; for 24h;	16 Specific embodiment sixteen: 44.2 mg (0.2 mmol) N-(2-(ethylthio)phenyl)but-3-enamide, 73.4 mg (0.56 mmol) 6-methylindole, 4.5 mg (0.02 mmol) palladium acetate as catalyst , 3.2 mg (0.02 mmol) of ferric chloride and 10.4 mg (0.06 mmol) of ferrous acetate as oxidants, and 29.3 mg (0.24 mmol) of benzoic acid as additives in 3 mL of solvent acetonitrile, and the reaction was stirred at 90 oC for 24 hours. After the reaction is cooled, the reaction solution is filtered to obtain a filtrate, and the solvent is removed from the filtrate with a rotary evaporator to obtain a residue. Wash, collect the effluent according to the actual gradient, detect through TLC, merge the effluent containing the target product, rotate the combined effluent to remove the solvent with a rotary evaporator, and vacuum dry to obtain a yellow solid γ, γ-diarylation product N-(2-(ethylthio)phenyl)-4,4-bis(6-methyl-1H-indol-3-yl)butanamide 75.1 mg, 78% yield.

Reference： [1]Current Patent Assignee: WENZHOU UNIVERSITY - CN113943244, 2022, A Location in patent: Paragraph 0028

85
[ 3420-02-8 ]
[ 637-59-2 ]
6-methyl-3-((3-phenylpropyl)selanyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With selenium; sodium t-butanolate In acetonitrile at 40℃; for 6h; Sealed tube;	3.1. 0.3 mmol scale General procedure: To a 8.0-mL scintillation vial equipped with a magnetic stirrer, indole 1a (0.36 mmol, 1.2 equiv.), selenium powder 2 (0.36 mmol, 1.2 equiv.), t-BuONa (0.45 mmol, 1.5 equiv.), solvent CH3CN (1.0 mL) and (3-bromopropyl)benzene 3a (0.30 mmol, 1.0 equiv.) sequentially added at room temperature. The vial was sealed with a screw-top septum cap and placed in a heating block that was preheated to 40 °C for 6h. After the indicated reaction time, an aqueous saturated NH4Cl solution and EtOAc were added and the layers were separated. The aqueous phase was extracted with EtOAc (x 3) and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: Petroleum ether/EtOAc) to give the target product 4aa as a Colorless oil.

Reference： [1]Cai, Zhong-Jian; Ji, Shun-Jun; Liu, Huan [Chinese Chemical Letters, 2022]

86
[ 3420-02-8 ]
[ 1198-30-7 ]
1-(6-methyl-1H-indol-1-yl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene In tetrahydrofuran; ethyl acetate at 20℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;

Reference： [1]Zhou, Chao; Gan, Qi-Chao; Zhou, Tai-Ping; Lei, Tao; Ye, Chen; He, Xiao-Jun; Chen, Bin; Lu, Heng; Wan, Qian; Liao, Rong-Zhen; Tung, Chen-Ho; Wu, Li-Zhu [Angewandte Chemie - International Edition, 2022, vol. 61, # 10][Angew. Chem., 2022, vol. 134, # 10]

87
[ 3420-02-8 ]
[ 1198-30-7 ]
1-(6-methyl-1H-indol-3-yl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,4-diaza-bicyclo[2.2.2]octane; 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene; di-tert-butyl phosphoric acid tetra-n-butylammonium salt In tetrahydrofuran; ethyl acetate at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;

88
[ 3420-02-8 ]
C₁₁H₁₂F₂O₃S [ No CAS ]
ethyl 2,2-difluoro-2-((6-methyl-1H-indol-3-yl)thio)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 6-methyl-1H-indole; C₁₁H₁₂F₂O₃S With trifluoromethylsulfonic anhydride In acetonitrile at 0℃; for 1h; Inert atmosphere; Stage #2: With diethylamine In acetonitrile at 0 - 20℃; for 12h; Inert atmosphere;	3 General procedure for difluoroalkylthiolation of arenes and heteroarenes General procedure: General procedure: To a mixture of arene or heteroarene 1 (0.2 mmol) and sulfoxide 2 (0.3 mmol,1.5 equiv) in MeCN (2.0 mL) was added trifluoromethanesulfonic anhydride (Tf2O, 50 μL, 0.3mmol, 1.5 equiv) at 0 oC. After stirring for 1 h, diethylamine (0.6 mmol, 3 equiv) was added. Theresulted reaction mixture was then gradually warmed to rt and kept stirring for 12 h. After that, the mixture was passed through a short silica gel column and concentrated under vacuum. The obtained residue was further purified by flash chromatography on silica gel affording product 3.

Reference： [1]Li, Kaixiao; Liang, Weijian; Zhang, Yage; Zhou, Lijiang [Synlett, 2022, vol. 33, # 6, p. 546 - 550]

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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 3420-02-8 ] {[proInfo.proName]}

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[ 3420-02-8 ] Synthesis Path-Upstream 1~6

[ 3420-02-8 ] Synthesis Path-Downstream 1~88

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