Name: 54136-25-3|5-Iodo-2,3,3-trimethyl-3H-indole|97%
Brand: Ambeed
SKU: A1373886
Price: 23.0 USD
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1
[ 54136-25-3 ]
[ 1484-88-4 ]
2-iodo-10,10-dimethyl-6,8-diphenyl-10H-pyrido[1,2-a]indolium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With sodium acetate In ethanol for 2h; Heating;

Reference： [1]Zimmermann, Thomas; Hennig, Lothar [Journal of Heterocyclic Chemistry, 2002, vol. 39, # 2, p. 263 - 269]

2
[ 563-80-4 ]
[ 13116-27-3 ]
[ 54136-25-3 ]

Yield	Reaction Conditions	Operation in experiment
97.08%	With sulfuric acid; In ethanol; for 12h;Reflux;	Example 4 Preparation of PC-005 Scheme 4 depicts a reaction pathway for the synthesis and labeling 64Cu labeled PET probe PC-005. Synthesis of diiodo-18: 5-Iodo-2,3,3-trimethylindolenine 16: A solution of <strong>[13116-27-3]4-iodophenylhydrazine</strong> 15 (1.37 g, 5.89 mmol), isopropylmethylketone (1.40 mL, 13.0 mmol), EtOH (20 mL) and concentrated H2SO4 (0.3 mL) was heated under reflux for 12 h. After being cooled to room temperature, the mixture was filtered and filtrate was added to distilled water (50 mL). The product was extracted with CH2Cl2 (250 mL). The combined organic layer was washed 10% NaHCO3 (250 mL) and (3*20 mL) distilled water, dried over sodium sulfate, filtered, and evaporated under reduced pressure to yield 16 (1.63 g, 97.08%) as a brownish liquid. mass spectrum (MALDI-TOF), m/z 286 (M+H).
96%	With acetic acid; In acetonitrile; for 4h;Reflux;	4-Iodophenylhydrazine (16.0 g, 68.36 mmol, 1 eq) was suspended in acetic acid (520 mL), then 3-methyl-2-butanone (8.06 mL, 75.20 mmol, 1.1 eq) was added and the reaction was heated at reflux for 4 h, cooled to room temperature and the solvent was removed under reduced pressure. The oily residue was dissolved in DCM and a large excess of hexane was added. The purple oil with solid impurities precipitated below the yellow hexane layer. The hexane layer was decanted off and the solvent was removed in vacuo to afford product 2 as a yellow oil in 96 % yield (18.65 g, 65.41mmol). Mw = 285.12 g/mol (C11H12IN).
76.5%	With acetic acid; for 3h;Reflux;	In the present example, a compound of the formula (III) was prepared by phenylhydrazine and 3-methyl-2-butanone..The p-iodophenylhydrazine (1.17 g, 5 mmol) and 3-methyl-2-butanone (0.52 g, 6 mmol) were dissolved in 30 ml of glacial acetic acid, and heated under reflux for 3 h to carry out a second reaction.After cooling to room temperature, the solvent was removed by rotary evaporation, and extracted with ethyl acetate and water, the product was extracted with anhydrous sodium sulfate, the solvent was removed by rotary evaporation,Further, purification with petroleum ether and ethyl acetate (2:1 by volume) afforded 1.09 g of the compound of the formula (III) as an orange oily liquid, having a purity of 98% and a yield of 76.5%

10.5 g

With acetic acid; for 20h;Reflux;

12.68g (54.1 mmol) of <strong>[13116-27-3](4-iodophenyl)hydrazine</strong> (1) and 8g (92.8 mmol) of 3-methyl-2-butanone were refluxed in 100 ml of glacial acetic acid for 20 hrs. The acetic was evaporated and the residue was dissolved in ether. Insoluble precipitate was filtered off and the etheric solution was washed with aqueous solution of NaOH followed by Na2S2O3 and water. The organic layer was dried with anhydrous Na2SO4 and the ether was removed under reduced pressure to afford 10.5g of 5-iodo-2,3,3-trimethyl-3H-indole (2) as red gummy liquid. H1 NMR (CDCl3): 7.60 (dd, J=4.5, 8.0 Hz, 2H, Ar-CH), 7.28 (d, J=8.0 Hz, 1H, ArCH), 2.25 (s, 3H, CH3), 1.20 (s, 6H, CH3X2). C13 NMR (CDCl3): 153.4 (C), 148.1 (C), 139.3 (C), 136.6 (CH), 130.6 (CH), 121.8 (CH), 89.9(C), 54.0 (C), 23.0 (CH3), 22.9 (CH3), 15.3 (CH3). ESMS (M+H+) Found=286.1, calculated for C11H12IN=285.12.

Reference： [1]Chemical Communications,2009,p. 4369 - 4371
[2]Patent: US2014/248213,2014,A1 .Location in patent: Paragraph 0285; 0290; 0291
[3]Journal of Organic Chemistry,2019,vol. 84,p. 1299 - 1309
[4]Tetrahedron,2012,vol. 68,p. 857 - 864
[5]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 263 - 269
[6]Dyes and Pigments,2017,vol. 136,p. 292 - 301
[7]Journal of Organic Chemistry,2008,vol. 73,p. 118 - 126
[8]Journal of Photochemistry and Photobiology A: Chemistry,2012,vol. 228,p. 51 - 59
[9]Patent: CN110128844,2019,A .Location in patent: Paragraph 0058-0062
[10]Chemistry - A European Journal,2019,vol. 25,p. 7998 - 8002
[11]Chemical Science,2019,vol. 10,p. 10586 - 10594
[12]Chemical Communications,2017,vol. 53,p. 2009 - 2012
[13]Journal of the American Chemical Society,2006,vol. 128,p. 15374 - 15375
[14]Chemical Communications,2008,p. 2004 - 2006
[15]Journal of the American Chemical Society,2011,vol. 133,p. 51 - 55
[16]Chemistry - A European Journal,2012,vol. 18,p. 10733 - 10741
[17]European Journal of Medicinal Chemistry,2016,vol. 113,p. 187 - 197
[18]Dyes and Pigments,2017,vol. 140,p. 6 - 13
[19]Patent: WO2017/89800,2017,A1 .Location in patent: Page/Page column 54; 55
[20]Bioconjugate Chemistry,2018,vol. 29,p. 1312 - 1318
[21]Chemistry - A European Journal,2018,vol. 24,p. 8841 - 8847

3
[ 54136-25-3 ]
[ 623-48-3 ]
[ 556836-52-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	at 85℃; for 12h;

Reference： [1]Jiao, Guan-Sheng; Loudet, Aurore; Lee, Hong Boon; Kalinin, Stanislav; Johansson, Lennart B.-Å.; Burgess, Kevin [Tetrahedron, 2003, vol. 59, # 17, p. 3109 - 3116]

4
[ 54136-25-3 ]
[ 74-88-4 ]
5-iodo-1,2,3,3-tetramethyl-3H-indol-1-ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Reflux;
81%	In acetonitrile for 12h; Sealed tube;
74%	In acetonitrile for 2h; Reflux;	3. Synthesis of 5-Iodo-1,2,3,3-tetramethyl-3H-indolium iodide (3) 5-Iodo-2,3,3-trimethylindolenine 2 (18.65 g, 65.41 mmol, 1 eq) was dissolved in acetonitrile (85 mL) then methyl iodide (4.90 mL, 78.49 mmol, 1.2 eq) was added and the reaction mixture was heated at reflux for 2 h. After cooling to room temperature the precipitate collected by filtration, washed with diethyl ether, and dried in vacuo. Product 3 was obtained as an orange solid in 74 % yield (20.59 g, 48.20 mmol). Mw = 427.06 g/mol (C12H15I2N).

2.33 g	In methanol at 110℃; for 6h;
1.71 g	In dichloromethane Reflux;
1.37 g	In methanol at 110℃; for 6h; Inert atmosphere; Sealed tube;
	In acetonitrile
0.29 g	In acetonitrile at 70℃;	1.2 Synthesis of Compound Q3 This compound Q3 was prepared according to the published procedure.2 The mixture of iso-propylmethyl ketone (0.66 g, 7.63 mmol) and para-iodophenyl hydrazine (1.05 g, 4.49 mmol) was refluxing under the catalysis of acetic acid (10 mL) in the N2 atmosphere for 5 h. After reaction, the solution diluted with H2O was neutral to pH=7 by NaHCO3. Then, the indole Q2 was extracted with ethyl acetate, yielding a brown oil (1.10 g, 3.86 mmol, 86% crude). And then Q2 reacted with iodomethane (0.87 g, 6.10 mmol) in acetonitrile (10 mL) under refluxing at 70°C overnight. The resulting precipitate was filtered, washed with diethyl ether to yield Q3 as a pink solid (0.29 g, 67%).
	In acetonitrile at 80℃; for 1.5h;

Reference： [1]Schulz-Senft, Mathias; Gates, Paul J.; Sönnichsen, Frank D.; Staubitz, Anne [Dyes and Pigments, 2017, vol. 136, p. 292 - 301]
[2]Ji, Yubin; Wang, Yali; Zhang, Na; Xu, Shengnan; Zhang, Leilei; Wang, Qinghua; Zhang, Qingyang; Hu, Hai-Yu [Journal of Organic Chemistry, 2019, vol. 84, # 3, p. 1299 - 1309]
[3]Gerowska, Marta; Hall, Lucy; Richardson, James; Shelbourne, Montserrat; Brown, Tom [Tetrahedron, 2012, vol. 68, # 3, p. 857 - 864]
[4]Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L. [Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15374 - 15375]
[5]Fegan, Adrian; Shirude, Pravin S.; Balasubramanian, Shankar [Chemical Communications, 2008, # 17, p. 2004 - 2006]
[6]Ueno, Yuichiro; Jose, Jiney; Loudet, Aurore; Perez-Bolivar, Cesar; Anzenbacher, Pavel; Burgess, Kevin [Journal of the American Chemical Society, 2011, vol. 133, # 1, p. 51 - 55]
[7]Li, Miao; Sun, Wen; Tian, Ruisong; Cao, Jianfang; Tian, Ye; Gurram, Bhaskar; Fan, Jiangli; Peng, Xiaojun [Biomaterials, 2021, vol. 269]
[8]Xu, Yuan; Tan, Yang; Ma, Xiuqin; Jin, Xiaoyi; Tian, Ye; Li, Miao [Molecules, 2021, vol. 26, # 19]
[9]Albitz, Evelin; Kern, Dóra; Kormos, Attila; Bojtár, Márton; Török, György; Biró, Adrienn; Szatmári, Ágnes; Németh, Krisztina; Kele, Péter [Angewandte Chemie - International Edition, 2022, vol. 61, # 6][Angew. Chem., 2022, vol. 134, # 6]

5
[ 540-37-4 ]
[ 54136-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / NaNO₂; SnCl₂ 2: acetic acid / 2.5 h / Heating
	Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water 2.1: acetic acid / 4 h / Reflux 2.2: pH 7
	Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -10 °C 1.2: 19.5 h / -10 - 5 °C 2.1: acetic acid / 20 h / Reflux

	Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -10 °C 1.2: -10 - 5 °C 2.1: acetic acid / 20 h / Reflux
	Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / 1.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: acetic acid / 3 h / 120 °C
	Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 1.2: 0.5 h / 0 °C 2.1: acetic acid / 3 h / Reflux
	Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 °C 1.2: 2 h / 20 °C 2.1: acetic acid / 4 h / Reflux
	Multi-step reaction with 2 steps 1: tin(ll) chloride; sodium nitrite 2: Acidic conditions
	Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -10 °C 1.2: 19.5 h / -10 - 5 °C 2.1: Reflux
	Multi-step reaction with 2 steps 1: hydrogenchloride; sodium nitrite 2: acetic acid
	Multi-step reaction with 2 steps 1: tin(II) chloride dihdyrate; hydrogenchloride; sodium nitrite / water / 1 h / -10 °C 2: acetic acid / 5 h / Inert atmosphere; Reflux

Reference： [1]Klotz, Eric J. F.; Claridge, Tim D. W.; Anderson, Harry L. [Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15374 - 15375]
[2]Chen, Jing; Winter, Rainer F. [Chemistry - A European Journal, 2012, vol. 18, # 34, p. 10733 - 10741]
[3]Atchison, Jordan; Kamila, Sukanta; Nesbitt, Heather; Logan, Kieran A.; Nicholas, Dean M; Fowley, Colin; Davis, James; Callan, Bridgeen; McHale, Anthony P; Callan, John F [Chemical Communications, 2017, vol. 53, # 12, p. 2009 - 2012]
[4]Current Patent Assignee: UNIVERSITY OF ULSTER - WO2017/89800, 2017, A1
[5]Knorr, Gergely; Kozma, Eszter; Schaart, Judith M.; Németh, Krisztina; Török, György; Kele, Péter [Bioconjugate Chemistry, 2018, vol. 29, # 4, p. 1312 - 1318]
[6]Kormos, Attila; Koehler, Christine; Fodor, Eszter A.; Rutkai, Zsófia R.; Martin, Madison E.; Mező, Gábor; Lemke, Edward A.; Kele, Péter [Chemistry - A European Journal, 2018, vol. 24, # 35, p. 8841 - 8847]
[7]Xu, Feng; Li, Haidong; Yao, Qichao; Ge, Haoying; Fan, Jiangli; Sun, Wen; Wang, Jingyun; Peng, Xiaojun [Chemical Science, 2019, vol. 10, # 45, p. 10586 - 10594]
[8]Lee, Se Hoon; Mergu, Naveen; Min, Kyeong Su; Satish Kumar, Rangaraju; Son, Young-A [Journal of Photochemistry and Photobiology A: Chemistry, 2020, vol. 397]
[9]Ebaston, T. M.; Gellerman, Gary; Nakonechny, Faina; Patsenker, Leonid; Talalai, Efrosiniia [Dyes and Pigments, 2021, vol. 184]
[10]Li, Miao; Sun, Wen; Tian, Ruisong; Cao, Jianfang; Tian, Ye; Gurram, Bhaskar; Fan, Jiangli; Peng, Xiaojun [Biomaterials, 2021, vol. 269]
[11]Xu, Yuan; Tan, Yang; Ma, Xiuqin; Jin, Xiaoyi; Tian, Ye; Li, Miao [Molecules, 2021, vol. 26, # 19]

6
[ 54136-25-3 ]
[ 556836-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / 12 h / 85 °C 2: 53 percent / CuI; 1,2-trans-diaminocyclohexane; Cs₂CO₃ / dioxane / 17 h / 100 °C

Reference： [1]Jiao, Guan-Sheng; Loudet, Aurore; Lee, Hong Boon; Kalinin, Stanislav; Johansson, Lennart B.-Å.; Burgess, Kevin [Tetrahedron, 2003, vol. 59, # 17, p. 3109 - 3116]

7
[ 54136-25-3 ]
C₅₈H₅₀N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / 12 h / 85 °C 2: 53 percent / CuI; 1,2-trans-diaminocyclohexane; Cs₂CO₃ / dioxane / 17 h / 100 °C 3: 66 percent / butan-1-ol; toluene / 16 h / Heating

Reference： [1]Jiao, Guan-Sheng; Loudet, Aurore; Lee, Hong Boon; Kalinin, Stanislav; Johansson, Lennart B.-Å.; Burgess, Kevin [Tetrahedron, 2003, vol. 59, # 17, p. 3109 - 3116]

8
[ 7772-99-8 ]
[ 540-37-4 ]
[ 54136-25-3 ]
[ 13116-27-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With hydrogenchloride; sodium nitrate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; water; toluene;	Sodium nitrate (16.56 g, 0.24 mol, Aldrich) dissolved in water (100 ml) was added dropwise within 45 mins. to a solution of 4-iodoaniline (43.9 g, 0.20 mol, Aldrich) in ice-water (600 ml) and concentrated hydrochloric acid (200 ml) which was cooled to 0-2 C. The reaction mixture was stirred for a further 30 minutess at 0-2 C. then tin(II) chloride (151.68 g, 0.8 mol, Aldrich) in c.HCl (150 ml) was added dropwise over 90 mins. while maintaining the temp. of the reaction mixture between 0-2 C. Following the addition, the resulting solution was warmed to room temperature and stirred for 3 hours. The yellow solid which had separated from the solution was then collected by filtration, placed in ice water (800 ml) and the pH adjusted to 10 with 25% aqueous potassium hydroxide solution. The resulting solid was collected by filtration, washed with a small amount of water and dried under vacuum. The product was then placed in toluene (400 ml) and filtered to remove insoluble impurities. Hexane (1200 ml) was added and upon cooling in the refrigerator yellow needles separated which were collected by filtration, washed with hexane (100 ml) and dried under high vacuum to give pure 4-Iodophenylhydrazine (23.36 g, 50%), m.p.=94 C. 5-Iodo-2,3,3-trimethyl-(3H)-indolenine (9) was prepared by a modification of the procedure of Moreau et al., Eur. J. Med. Chem. Chim. Ther., 9 (3): 274-280 (1974).

Reference： [1]Patent: US5667764,1997,A

9
[ 54136-25-3 ]
[ 75-03-6 ]
C₁₃H₁₈IN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	at 90℃; for 3h;	10 A mixture of 5-iodo-2,3,3-trimethyl-3H-indolenine (2.0 g, 7.0 mmol) and ethyliodide (1.76 ml, 3.42 g, 22 mmol) was heated at +90°C for 3 h. The reaction mixture wascooled and triturated with ether. Solid material was filtered off, washed with ether and driedin vacuum to give desired product (2.45 g, 79%) as pink solid. *H NMR (dmso-d6): 8 8.31 (s,1H), 8.00 (d, J=8.4 Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 4.46 (q, J=7.4 Hz, 2H), 2.80 (s, 3H),1.52 (s 6H), 1.41 (t, J=7.2 Hz, 3H).

Reference： [1]Current Patent Assignee: PAI PARTNERS - WO2006/20947, 2006, A2 Location in patent: Page/Page column 80-81

10
[ 1120-71-4 ]
[ 54136-25-3 ]
[ 876746-21-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	at 100℃; for 0.5h;	9 A mixture of 5-iodo-2,3,3-trimethyl-3H-indolenine (Eur. J. Med. Chem. Chim.Ther. 1974, 9(3), 274-280) (4.74 g, 16.6 mmol) and propanesultone (2.0 g, 16.4 mmol) washeated at +100°C for 30 min. The reaction mixture was cooled and triturated with ether.Solid material was filtered off, washed with ether, dichloromethane and dried in vacuum togive desired product (5.5 g, 82%) as off-white solid.

Reference： [1]Current Patent Assignee: PAI PARTNERS - WO2006/20947, 2006, A2 Location in patent: Page/Page column 79

11
[ 54136-25-3 ]
[ 67899-04-1 ]
C₂₁H₃₂INO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	at 90℃; for 9h;	10 A mixture of 5-iodo-2,3,3-trimethyl-3H-indolenine (Eur. J. Med. Chem. Chim.Ther. 1974, 9(3), 274-280) (1.0 g, 3.5 mmol) and tert-butyl 6-iodohexanoate (1.382 g, 4.6mmol) was heated at +90°C for 9 h. The reaction mixture was cooled and triturated withether. Solid material was filtered off, washed with ether and dried in vacuum to give desiredproduct (1.2 g, 59%) as pale pink solid. *H NMR (dmso-d6): 5 8.31 (s, 1H), 8.00 (d, J=8.4Hz, 1H), 7.80 (d, J=8.4 Hz, 1H), 4.42 (t, J=7.4 Hz, 2H), 3.91 (bs, 2H), 2.81 (s, 3H), 2.19 (t,J=7.2 Hz, 2H), 1.80 (qn, J=7.0 Hz, 2H), 1.53 (s, 6H), 1.50 (qn, J=7.2 Hz, 2H), 1.36 (s, 9H).

Reference： [1]Current Patent Assignee: PAI PARTNERS - WO2006/20947, 2006, A2 Location in patent: Page/Page column 80

12
[ 54136-25-3 ]
[ 2973-19-5 ]
[ 1005213-60-4 ]

Yield	Reaction Conditions	Operation in experiment
41%	In acetonitrile for 72h; Heating;

Reference： [1]Tomasulo, Massimiliano; Sortino, Salvatore; Raymo, Francisco M. [Journal of Organic Chemistry, 2008, vol. 73, # 1, p. 118 - 126]

13
[ 54136-25-3 ]
[ 333-27-7 ]
[ 1187043-11-3 ]

Yield	Reaction Conditions	Operation in experiment
91.2%	In acetonitrile for 8h; Reflux; Inert atmosphere;
73.8%	In acetonitrile for 8h; Inert atmosphere; Reflux;

Reference： [1]Kumar, Satish; Watkins, Davita L.; Fujiwara, Tomoko [Chemical Communications, 2009, # 29, p. 4369 - 4371]
[2]Location in patent: experimental part Watkins, Davita L.; Fujiwara, Tomoko [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 51 - 59]

14
[ 54136-25-3 ]
5-carboxy-2-[[3-[(1,3-dihydro-5-iodo-3,3-dimethyl-1-octyl-2Hindol-2-ylidene)methyl]-2-hydroxy-4-oxo-2-cyclobuten-1-ylidene]methyl]-3,3-dimethyl-1-octyl-3H-indolium, inner salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetonitrile / 60 h / Reflux; Inert atmosphere 2: triethylamine / ethanol / 1 h / Reflux; Inert atmosphere 3: water; sodium hydroxide / ethanol / 0.17 h / Reflux 4: <i>tert</i>-butyl alcohol; benzene / 19 h / Reflux

Reference： [1]Warnan, Julien; Buchet, Fabien; Pellegrin, Yann; Blart, Errol; Odobel, Fabrice [Organic Letters, 2011, vol. 13, # 15, p. 3944 - 3947]

15
[ 54136-25-3 ]
C₂₅H₃₂INO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetonitrile / 60 h / Reflux; Inert atmosphere 2: triethylamine / ethanol / 1 h / Reflux; Inert atmosphere

Reference： [1]Warnan, Julien; Buchet, Fabien; Pellegrin, Yann; Blart, Errol; Odobel, Fabrice [Organic Letters, 2011, vol. 13, # 15, p. 3944 - 3947]

16
[ 54136-25-3 ]
[ 1314033-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 60 h / Reflux; Inert atmosphere 2: triethylamine / ethanol / 1 h / Reflux; Inert atmosphere 3: water; sodium hydroxide / ethanol / 0.17 h / Reflux

Reference： [1]Warnan, Julien; Buchet, Fabien; Pellegrin, Yann; Blart, Errol; Odobel, Fabrice [Organic Letters, 2011, vol. 13, # 15, p. 3944 - 3947]

17
[ 54136-25-3 ]
[ 629-27-6 ]
[ 1314033-61-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetonitrile for 60h; Reflux; Inert atmosphere;

Reference： [1]Warnan, Julien; Buchet, Fabien; Pellegrin, Yann; Blart, Errol; Odobel, Fabrice [Organic Letters, 2011, vol. 13, # 15, p. 3944 - 3947]

18
[ 54136-25-3 ]
[ 542-69-8 ]
[ 930102-07-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	In acetonitrile for 24h; Reflux;	4. Synthesis of 1-Buthyl-5-iodo-2,3,3-trimethyl-3H-indolium iodide (4) 5-Iodo-2,3,3-trimethylindolenine 2 (6.71 g, 23.54 mmol, 1 eq) was dissolved in acetonitrile (60 mL) then 1-iodobutane (21.43 mL, 188.30 mmol, 8 eq) was added and the reaction mixture heated at reflux for 24 h. After the reaction was cooled to room temperature, the precipitate was collected by filtration, washed with diethyl ether, and dried in vacuo. Product 4 was obtained as pink crystals with 94 % yield (10.33 g, 22.03 mmol). Mw = 469.14 g/mol (C15H21I2N).
	In acetonitrile at 155℃; for 0.583333h; Sealed tube; Microwave irradiation;	4.1.1 Synthesis General procedure: The starting 5-substitute 2,3,3-trimethylindolium (2a-b) was readily obtained via the condensation of benzohydrazine substitute 1a-b with 3-methylbutan-2-one in glacial acetic, acid as previously reported [15,16] (see Scheme 2). The obtained indolenines were then quaternarized. In a typical experiment, an appropriate iodo-alkane (1:4 M ratio) was placed into a reaction vial with CH3CN and 2a-b. The vessel was then sealed with a crimp cap and heated in the microwave system at 155 °C for 35 min, according to a previously published procedure [15]. The solid formed was isolated by filtration and repeatedly washed under stirring with diethyl ether (3 × 200 ml) and then filtered, giving pure products 3a-b.
	In acetonitrile

Reference： [1]Gerowska, Marta; Hall, Lucy; Richardson, James; Shelbourne, Montserrat; Brown, Tom [Tetrahedron, 2012, vol. 68, # 3, p. 857 - 864]
[2]Serpe, Loredana; Ellena, Silvano; Barbero, Nadia; Foglietta, Federica; Prandini, Federica; Gallo, Maria Pia; Levi, Renzo; Barolo, Claudia; Canaparo, Roberto; Visentin, Sonja [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 187 - 197]
[3]Saikiran, Maryala; Sato, Daisuke; Pandey, Shyam S.; Ohta, Takeshi; Hayase, Shuzi; Kato, Tamaki [Dyes and Pigments, 2017, vol. 140, p. 6 - 13]

19
[ 54136-25-3 ]
[ 1364234-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium hydroxide / water / 0.25 h / 20 °C 3: trichloroethane / 12 h / Inert atmosphere; Reflux 4: 1-Methylpyrrolidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / 12 h / 85 °C / Inert atmosphere

Reference： [1]Watkins, Davita L.; Fujiwara, Tomoko [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 51 - 59]

20
[ 54136-25-3 ]
[ 1364234-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium hydroxide / water / 0.25 h / 20 °C 3: trichloroethane / 12 h / Inert atmosphere; Reflux 4: 1-Methylpyrrolidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / 12 h / 85 °C / Inert atmosphere

Reference： [1]Watkins, Davita L.; Fujiwara, Tomoko [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 51 - 59]

21
[ 54136-25-3 ]
5-iodo-1,3,3-trimethyl-2-methylene-2,3-dihydro-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium hydroxide / water / 0.25 h / 20 °C

Reference： [1]Watkins, Davita L.; Fujiwara, Tomoko [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 51 - 59]

22
[ 54136-25-3 ]
5-iodo-1,3,3-trimethylspiro[indoline-[2,3']-naphtho[2,1-b][1,4]oxazine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium hydroxide / water / 0.25 h / 20 °C 3: trichloroethane / 12 h / Inert atmosphere; Reflux

Reference： [1]Watkins, Davita L.; Fujiwara, Tomoko [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 51 - 59]

23
[ 18742-02-4 ]
[ 54136-25-3 ]
[ 1397291-88-1 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium iodide In acetonitrile for 45h; Reflux;

Reference： [1]Hall, Lucy M.; Gerowska, Marta; Brown, Tom [Nucleic Acids Research, 2012, vol. 40, # 14, p. e108]

24
[ 54136-25-3 ]
[ 75-03-6 ]
[ 1402436-18-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetonitrile at 70℃; for 12h;	3.2 Example 3.2 To compound 3.1 (0.500g, 1.75mmol, 1.0eq) was added to 15mL of acetonitrile, iodomethane (1.37g, 8.77mmol, 5.0eq) was added, the reaction was carried out at 70°C for 12h, the reaction was stopped, cooled to room temperature, and added into 100 mL of diethyl ether, the precipitate was collected to give compound 3.2 (0.58 g, 1.31 mmol, Y=75.0%).
71%	In acetonitrile for 48h; Inert atmosphere; Reflux;
69.1%	In toluene for 6h; Reflux;

	In acetonitrile at 155℃; for 0.583333h; Sealed tube; Microwave irradiation;	4.1.1 Synthesis General procedure: The starting 5-substitute 2,3,3-trimethylindolium (2a-b) was readily obtained via the condensation of benzohydrazine substitute 1a-b with 3-methylbutan-2-one in glacial acetic, acid as previously reported [15,16] (see Scheme 2). The obtained indolenines were then quaternarized. In a typical experiment, an appropriate iodo-alkane (1:4 M ratio) was placed into a reaction vial with CH3CN and 2a-b. The vessel was then sealed with a crimp cap and heated in the microwave system at 155 °C for 35 min, according to a previously published procedure [15]. The solid formed was isolated by filtration and repeatedly washed under stirring with diethyl ether (3 × 200 ml) and then filtered, giving pure products 3a-b.
	at 120℃; for 0.5h; Microwave irradiation;
	In acetonitrile Reflux;
	In acetonitrile at 80℃; for 16h;
	In acetonitrile for 12h; Reflux;	1.3; 2.3; 3.3 (3) Synthesis of indole iodonium salt: 5-Iodo-2,3,3-trimethyl-3H-indole (0.5710 g, 2.00 mmol) and iodoethane (0.5 mL, 6.25 mmol) were dissolved in 5 mL of acetonitrile and refluxed for 12 h.After cooling to 0°C, the filter residue was collected by filtration to obtain the crude product, which was then washed three times with a mixed solvent of ethanol and dichloromethane (1/5, Ve/Vd),A purple solid product is obtained, referred to as indole iodonium salt for short.

Reference： [1]Current Patent Assignee: UNIV DALIAN TECH - CN114591632, 2022, A Location in patent: Paragraph 0075; 0081-0083
[2]Chen, Jing; Winter, Rainer F. [Chemistry - A European Journal, 2012, vol. 18, # 34, p. 10733 - 10741]
[3]Xu, Feng; Li, Haidong; Yao, Qichao; Ge, Haoying; Fan, Jiangli; Sun, Wen; Wang, Jingyun; Peng, Xiaojun [Chemical Science, 2019, vol. 10, # 45, p. 10586 - 10594]
[4]Serpe, Loredana; Ellena, Silvano; Barbero, Nadia; Foglietta, Federica; Prandini, Federica; Gallo, Maria Pia; Levi, Renzo; Barolo, Claudia; Canaparo, Roberto; Visentin, Sonja [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 187 - 197]
[5]Knorr, Gergely; Kozma, Eszter; Schaart, Judith M.; Németh, Krisztina; Török, György; Kele, Péter [Bioconjugate Chemistry, 2018, vol. 29, # 4, p. 1312 - 1318]
[6]Kormos, Attila; Koehler, Christine; Fodor, Eszter A.; Rutkai, Zsófia R.; Martin, Madison E.; Mező, Gábor; Lemke, Edward A.; Kele, Péter [Chemistry - A European Journal, 2018, vol. 24, # 35, p. 8841 - 8847]
[7]Albitz, Evelin; Kern, Dóra; Kormos, Attila; Bojtár, Márton; Török, György; Biró, Adrienn; Szatmári, Ágnes; Németh, Krisztina; Kele, Péter [Angewandte Chemie - International Edition, 2022, vol. 61, # 6][Angew. Chem., 2022, vol. 134, # 6]
[8]Current Patent Assignee: TIANJIN POLYTECHNIC UNIVERSITY - CN113956242, 2022, A Location in patent: Paragraph 0109; 0116-0117; 0124; 0132-0133; 0138; 0146-0147

25
[ 54136-25-3 ]
2,4-bis[(5-iodo-1-ethyl-3,3-dimethylindolin-2-ylidene)methyl]cyclobutene-diylium-1,3-diiolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 48 h / Inert atmosphere; Reflux 2: sodium hydroxide / water; toluene / 5 h 3: benzene; isopropyl alcohol / 21 h / Reflux
	Multi-step reaction with 2 steps 1: acetonitrile / 0.58 h / 155 °C / Sealed tube; Microwave irradiation 2: butan-1-ol; toluene / 0.5 h / 160 °C / Microwave irradiation

Reference： [1]Chen, Jing; Winter, Rainer F. [Chemistry - A European Journal, 2012, vol. 18, # 34, p. 10733 - 10741]
[2]Serpe, Loredana; Ellena, Silvano; Barbero, Nadia; Foglietta, Federica; Prandini, Federica; Gallo, Maria Pia; Levi, Renzo; Barolo, Claudia; Canaparo, Roberto; Visentin, Sonja [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 187 - 197]

26
[ 54136-25-3 ]
[ 1266617-86-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With indium; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;

Reference： [1]Lee, Sungmin; Ji, Seungwook; Kang, Young Jong [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 11, p. 3740 - 3744]

27
[ 54136-25-3 ]
[ 3779-42-8 ]
C₁₇H₂₇IN₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 72h;Reflux;	General procedure: Individual 2,3,3-indolenine heterocyclic precursors 8-14 was dissolved in anhydrous acetonitrile (50 mL) and was heated to 40 C followed by the addition of the appropriate alkylating agent in 3 molar excess and was then heated to reflux for 72 h. The reaction progress was followed by TLC eluting with DCM/methanol/acetic acid (40/58/2). The reaction mixture was allowed to cool and the solvent was partially removed in vacuo. The final compounds were obtained by precipitation from methanol by diluting with acetone, ethyl acetate and diethyl ether. The hygroscopic compounds were allowed to dry for several hours under high vacuum.

Reference： [1]Molecules,2013,vol. 18,p. 13588 - 13607

28
[ 563-80-4 ]
[ 62830-55-1 ]
[ 54136-25-3 ]

Reference： [1]Journal of Materials Chemistry C,2016,vol. 4,p. 3138 - 3142
[2]Molecules,2013,vol. 18,p. 13588 - 13607

29
[ 54136-25-3 ]
[ 4224-70-8 ]
1-(5-carboxypentyl)-5-iodo-2,3,3-trimethyl-3H-indol-1-ium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	at 90℃; for 48h; Sealed tube;	1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium bromide (3a): General procedure: 2,3,3-Trimethyl-3H-indole (1.0g, 6.3mmol) was mixed with 6-bromohexanoic acid (1.84g, 9.4mmol) and heated at 120°C for 15h in a sealed tube. The reaction mixture was cooled to RT, diluted with benzene (5mL), the solvent was decanted, and the residue was triturated with benzene (3×5mL), and filtered. The obtained precipitate was washed with acetone (1mL) and dried to yield 3a (1.33g, 60%).
	at 110℃; for 8h;	3 A solution of 5-iodo-2,3,3-trimethylindolenine 16 and 6-bromohexanoic acid 2 was heated at 110° C. for 8 hrs to produce 1-(5′-carboxypentyl)-5-iodo-2,3,3-trimethylindolinium bromide 17. The compound 17 (100 mg, 0.21 mmol) was mixed with N-[5-anilino-3-chloro-2,4-(propane-1′,3′-diyl)-2,4-pentadien-1-ylidene]anilinium chloride 4 (37.4 mg, 0.105 mmol) and sodium acetate (40 mg, 0.49 mmol) in 20 mL of ethanol and the solution was refluxed for 12 min. The solution was then concentrated to dryness and the residue was trituated twice with 5 ml of 2N HCl. The residue was dried under vacuum to yield diiodo 18 as dark solid. mass spectrum (MALDI-TOF), m/z 937.2 (M+H).
	In acetonitrile at 85℃; for 60h;	2.2.3. Synthesis of 1-(5-carboxypentyl)-5-chloro-2,3,3-trimethyl-3H-indol-1-ium (6c) General procedure: In 100 mL double-necked flask, 5-chloro-2,3,3-trimethyl-3H-indole(6b) (3.13 g, 16.2 mmol) and 6-bromohexanoic acid (3 mL, 21.7 mmol) were dissolved in 30 mL of acetonitrile. The mixture was refluxedat 85 C for 60 h under shading. Then, the mixture was cooled to roomtemperature and evaporated in vacuum. The crude material was purifiedby normal phase flash chromatography with CH2Cl2: MeOH (15:1 v/v)for 6c to obtain a purple liquid (3.67 g, 73.4%).

Reference： [1]Gellerman, Gary; Kobzev, Dmytro; Kolosova, Olga; Nakonechny, Faina; Patsenker, Leonid; Semenova, Olga; Tatarets, Anatoliy; Yazbak, Fares [Dyes and Pigments, 2021, vol. 195]
[2]Current Patent Assignee: UNIVERSITY OF VIRGINIA; CEDARS-SINAI HEALTH SYSTEM - US2014/248213, 2014, A1 Location in patent: Paragraph 0285; 0291
[3]Liu, Hao; Yin, Juanjuan; Xing, Enyun; Du, Yingying; Su, Yu; Feng, Yaqing; Meng, Shuxian [Dyes and Pigments, 2021, vol. 190]

30
[ 54136-25-3 ]
[ 488-86-8 ]
3-(5-iodo-3,3-dimethyl-1,3-dihydro-indol-2-ylidenemethyl)-5-(5-iodo-3,3-dimethyl-3H-indol-2-ylmethylene)-4-hydroxy-cyclopent-3-ene-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In toluene; butan-1-ol at 110℃; for 3h; Dean-Stark;

Reference： [1]Punzi; Capozzi; Fino; Carlucci; Suriano; Mesto; Schingaro; Orgiu; Bonacchi; Leydecker; Samorì; Musio; Farinola, Gianluca Maria [Journal of Materials Chemistry C, 2016, vol. 4, # 15, p. 3138 - 3142]

31
[ 54136-25-3 ]
C₂₃H₂₅BF₂N₂O [ No CAS ]
C₃₄H₃₅BF₂IN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With trifluoroacetic acid In ethanol for 12h; Reflux;

Reference： [1]Zhang, Yang; Tang, Sicheng; Sansalone, Lorenzo; Baker, James D.; Raymo, Françisco M. [Chemistry - A European Journal, 2016, vol. 22, # 42, p. 15027 - 15034]

32
[ 54136-25-3 ]
[ 2892-51-5 ]
C₂₆H₂₂I₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In toluene; butan-1-ol at 160℃; for 0.5h; Microwave irradiation;	4.1.1 Synthesis General procedure: The starting 5-substitute 2,3,3-trimethylindolium (2a-b) was readily obtained via the condensation of benzohydrazine substitute 1a-b with 3-methylbutan-2-one in glacial acetic, acid as previously reported [15,16] (see Scheme 2). The obtained indolenines were then quaternarized. In a typical experiment, an appropriate iodo-alkane (1:4 M ratio) was placed into a reaction vial with CH3CN and 2a-b. The vessel was then sealed with a crimp cap and heated in the microwave system at 155 °C for 35 min, according to a previously published procedure [15]. The solid formed was isolated by filtration and repeatedly washed under stirring with diethyl ether (3 × 200 ml) and then filtered, giving pure products 3a-b. (0023) A suspension of squaric acid (0.5 mmol) and either indolenine or indolium molecules 3 (1 mmol) in a 1:1 mixture of butanol:toluene (2 ml) was heated at 160 °C in the microwave reactor. The deep blue-green mixture was cooled to room temperature and a shiny purple precipitate was formed. The solvent was removed and the precipitate was washed a few times with diethyl ether. Squaraines were obtained in 41-82% yields.

Reference： [1]Serpe, Loredana; Ellena, Silvano; Barbero, Nadia; Foglietta, Federica; Prandini, Federica; Gallo, Maria Pia; Levi, Renzo; Barolo, Claudia; Canaparo, Roberto; Visentin, Sonja [European Journal of Medicinal Chemistry, 2016, vol. 113, p. 187 - 197]

33
[ 1633-83-6 ]
[ 54136-25-3 ]
5-iodo-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indol-1-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In toluene for 18h; Reflux;
8 g	In toluene for 18h; Reflux;	11 Synthesis of 5-iodo-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indol-1-ium (3) Toluene (70 ml), 5-iodo-2,3,3-trimethyl-3H-indole (2) (12g, 42.1 mmol) and 1,4-butane sultone (8.6g, 63.1 mmol) were heated under reflux for 18 hrs. The reaction mixture was allowed to cool to room temperature. The resulting brown crystals were filtered and washed with acetone (3x10 ml). The filtered product was recrystallized from a solution of MeOH and diethyl ether. The crystals were collected and dried in vacuo to yield 8g of 5-iodo-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indol-1-ium (3). H1 NMR (dmso-d6): 8.27 (s, 1H, Ar-CH), 7.95 (s, 1H, Ar-CH), 7.82(s, 1H, Ar-CH), 4.42 (brs, 2H, CH2), 2.79 (s, 3H, CH3), 2.47 (brs, 2H, CH2), 1.90 (brs, 2H, CH2), 1.69 (brs, 2H,CH2), 1.49 (s, 6H, CH3X2). C13 NMR (DMSO-d6): 176.2, 148.4, 139.9, 136.7, 132.5, 126.8, 96.8, 49.8, 46.8, 42.6, 26.8, 25.6, 10.5. ESMS (M+H+) Found=422.10, calculated for C15H21FNO3S+=422.30.

Reference： [1]Atchison, Jordan; Kamila, Sukanta; Nesbitt, Heather; Logan, Kieran A.; Nicholas, Dean M; Fowley, Colin; Davis, James; Callan, Bridgeen; McHale, Anthony P; Callan, John F [Chemical Communications, 2017, vol. 53, # 12, p. 2009 - 2012]
[2]Current Patent Assignee: UNIVERSITY OF ULSTER - WO2017/89800, 2017, A1 Location in patent: Page/Page column 54; 55; 56

34
[ 54136-25-3 ]
[ 5029-66-3 ]
C₁₅H₁₉INO₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In acetonitrile for 48h; Reflux;	First, methyl 3-bromopropionate (20g, 0.12mol)And sodium iodide (40g, 0.24mol)Passing Finkelstein in acetoneMethod for synthesizing methyl 3-iodopropionate (product a);Synthesis of 5-iodo-2,3,3-trimethyl-3H-indole (product b) (6 g, 49.3%) by the method of Reference 1;Then a and b were dissolved in acetonitrile and heated to reflux for 48 hours.Column chromatography5-iodo-1-(3-methoxy-3-isopropyl)-2,3,3-trimethyl-3H- indole-1-Iodide (product c) (2.5 g, 64%);Dissolve c in methanol,After reacting with an aqueous solution of lithium hydroxide at 40 ° C for 8 hours,Column chromatography gave 1-(2-carboxyethyl)-5-iodo-2,3,3-trimethyl-3H-indole-1-iodide (product d) (1 g, 41.67%);At 0 ° C,With acetic anhydride (110 mg, 1.08 mmol)In dichloromethane (1 mL) solution pentadienal dipropylene aniline hydrochloride(284 mg, 1 mmol) and N,N-diisopropylethylamine (500 mg, 3.9 mmol)Mix in dichloromethane (3mL) solution,It was stirred at room temperature for 3 hours.The solvent was removed by rotary evaporation in vacuo and replaced with ethanol.D (640 mg, 1.79 mmol) and sodium acetate(730 mg) of ethanol (5 ml)The suspension is added to the above solution,The mixture was stirred at 80 ° C overnight.Concentrated by vacuum rotary evaporation,Purification by column chromatography gave a green solid.That is the final product CyI (200mg, 25.7%)

Reference： [1]Current Patent Assignee: QINGDAO UNIVERSITY - CN108624080, 2018, A Location in patent: Paragraph 0008; 0022

35
[ 54136-25-3 ]
5-(4-aminophenyl)-2-((1E,3E)-5-((E)-1-(5-carboxypentyl)-3,3-dimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetonitrile / 12 h / Sealed tube 2.1: acetic acid / acetic anhydride / 2 h / 130 °C / Reflux 2.2: 2 h / 120 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; water / 1,4-dioxane / 1.5 h / 90 °C
	Multi-step reaction with 4 steps 1.1: acetonitrile / 12 h / Sealed tube 2.1: acetic acid / acetic anhydride / 2 h / 130 °C / Reflux 2.2: 2 h / 120 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; water / 1,4-dioxane / 1.5 h / 90 °C 4.1: NADH / dimethyl sulfoxide / 1 h / 37 °C / pH 7.4 / Enzymatic reaction
	Multi-step reaction with 4 steps 1.1: acetonitrile / 12 h / Sealed tube 2.1: acetic acid / acetic anhydride / 2 h / 130 °C / Reflux 2.2: 2 h / 120 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; water / 1,4-dioxane / 1.5 h / 90 °C 4.1: NADH / dimethyl sulfoxide / 1 h / 37 °C / pH 7.4 / Enzymatic reaction

Reference： [1]Ji, Yubin; Wang, Yali; Zhang, Na; Xu, Shengnan; Zhang, Leilei; Wang, Qinghua; Zhang, Qingyang; Hu, Hai-Yu [Journal of Organic Chemistry, 2019, vol. 84, # 3, p. 1299 - 1309]
[2]Ji, Yubin; Wang, Yali; Zhang, Na; Xu, Shengnan; Zhang, Leilei; Wang, Qinghua; Zhang, Qingyang; Hu, Hai-Yu [Journal of Organic Chemistry, 2019, vol. 84, # 3, p. 1299 - 1309]
[3]Ji, Yubin; Wang, Yali; Zhang, Na; Xu, Shengnan; Zhang, Leilei; Wang, Qinghua; Zhang, Qingyang; Hu, Hai-Yu [Journal of Organic Chemistry, 2019, vol. 84, # 3, p. 1299 - 1309]

36
[ 54136-25-3 ]
[ 25291-17-2 ]
(E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-en-1-yl)-3H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrabutylammomium bromide; sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere;

Reference： [1]Braun, Alexander B.; Wehl, Ilona; Kölmel, Dominik K.; Schepers, Ute; Bräse, Stefan [Chemistry - A European Journal, 2019, vol. 25, # 34, p. 7998 - 8002]

37
[ 54136-25-3 ]
[ 19430-93-4 ]
(E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)-3H-indole [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 7998 - 8002

38
[ 54136-25-3 ]
[ 25431-45-2 ]
(E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoronon-1-en-1-yl)-3H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With tetrabutylammomium bromide; sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 20h; Inert atmosphere;

Reference： [1]Braun, Alexander B.; Wehl, Ilona; Kölmel, Dominik K.; Schepers, Ute; Bräse, Stefan [Chemistry - A European Journal, 2019, vol. 25, # 34, p. 7998 - 8002]

39
[ 54136-25-3 ]
[ 2892-51-5 ]
C₂₆H₂₄I₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.1%	In toluene; butan-1-ol for 3h; Dean-Stark; Inert atmosphere;	2 Example 2 In the present embodiment, a compound (SQ) having a structure represented by the formula (II) is produced by a compound of the structure represented by the formula (III) and a squaric acid.Under a nitrogen atmosphere, in a Dean-Stark apparatus, squaric acid (0.11 g, 1 mmol) was placed in 10 ml of n-butanol and 10 ml of toluene, and heated under reflux for 1 h.The squaric acid is dissolved in a binary solvent system to obtain a reaction liquid.The compound of the formula (III) (0.57 g, 2 mmol) was dissolved in 5 ml of n-butanol and 5 ml of toluene, and the reaction mixture was added dropwise thereto, and the reaction was stopped after the first reaction for 3 hours.The first reaction product is cooled to precipitate a solid precipitate, and the precipitate is washed by adding n-hexane to filter, and then the precipitate is subjected to dissolution extraction by adding dichloromethane and water.After drying with anhydrous sodium sulfate, rotary evaporation, and purification with a mixed solution of dichloromethane and petroleum ether in a volume ratio of 1:1.The green solid product, 446.1 mg of the compound of the formula (II), was obtained with a purity of 99% and a yield of 68.1%

Reference： [1]Current Patent Assignee: GUANGDONG UNIVERSITY OF TECHNOLOGY - CN110128844, 2019, A Location in patent: Paragraph 0063-0067

40
[ 54136-25-3 ]
C₁₈H₂₅BO₂ [ No CAS ]
C₂₂H₂₅NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5-iodo-2,3,3-trimethyl-3H-indole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 3-buten-1-ol benzoate; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 3.16667h; Inert atmosphere; Stage #2: C₁₈H₂₅BO₂	Indolenine benzoate 2 To a flask containing 3-buten-l-ol benzoate (3.0 g, 17.1 mmol) was added a 0.5 M solution of 9-borabicyclo[3.3.l]nonane (34.1 mL, 17.1 mmol) in THF. The clear, colorless solution was stirred at room temperature for 3 hours. In a separate flask fitted with a condenser was charged iodo indolenine (1, 3.4 g, 11.9 mmol), [l,l'-Bis(diphenylphosphino) ferrocene]palladium(II) dichloride (0.7 g, 0.8 mmol), and cesium chloride (6.0 g, 18.5 mmol). DMF (20 mL) was charged to the flask and the dark suspension was sparged with argon for 10 minutes. After addition of the benzoate borane/THF solution the reaction was heated to 70°C for 12 hours. After this time HPLC indicated complete conversion of the starting indolenine 1. The reaction was cooled to room temperature, diluted with EtOAc (50 mL) and hexanes (50 mL), and filtered through celite. The organic layer was washed water (3x), bring, and dried over magnesium sulfate. After filtration and evaporation the crude residue was purified by normal phase chromatography (050% EtO Ac/hexanes, Si02), affording indolenine 2 (3.0 g, 75% yield) as a viscous yellow oil. HRMS (ESI) calculated for C22H26NO2 (M+H)+ 336.1964, observed 336.1962

Reference： [1]Current Patent Assignee: 4CATALYZER CORPORATION - WO2020/14681, 2020, A1 Location in patent: Paragraph 00308

41
[ 54136-25-3 ]
2-(2-{2-chloro-3-[2-(5-iodo-1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylidene]-cyclohex-1-enyl}-vinyl)-5-iodo-1,3,3-trimethyl-3H-indolium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 2 h / 80 °C 2: sodium acetate / 4 h / 50 °C / Inert atmosphere

Reference： [1]Ebaston, T. M.; Gellerman, Gary; Nakonechny, Faina; Patsenker, Leonid; Talalai, Efrosiniia [Dyes and Pigments, 2021, vol. 184]

42
[ 54136-25-3 ]
[ 74-88-4 ]
5-iodo-1,2,3,3-tetramethyl-3H-indolium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In toluene at 80℃; for 2h;	General procedure for the synthesis of 1,2,3,3-tetramethyl-3H-indolium (3a), 5-iodo-1,2,3,3-tetramethyl-3H-indolium (3b) and 4,6-diiodo-1,2,3,3-tetramethyl-3H-indolium (3c) General procedure: 3a, 3b, 3c were synthesized according to the procedure [23]. Corresponding indolenine 2a-2c (1g, 500mg and 500mg, respectively, 6.3, 1.8 and 1.2mmol) was dissolved in toluene (1mL) and a large excess of methyl iodide (3 eq.) was added. The reaction mixture was heated in a pressure tube at 80°C for 2h, cooled to RT, and the precipitate was filtered and dried in a vacuum desiccator. Yields 760mg (70%) (3a); 289mg (55%) (3b); 222mg (43%) (3c).

Reference： [1]Ebaston, T. M.; Gellerman, Gary; Nakonechny, Faina; Patsenker, Leonid; Talalai, Efrosiniia [Dyes and Pigments, 2021, vol. 184]

43
[ 10273-89-9 ]
[ 54136-25-3 ]
2,3,3-trimethyl-5-[3-methyl-2-(pyridin-2-yl)phenyl]-3H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With (p-cymene)ruthenium diacetate; potassium carbonate In 1,4-dioxane at 30 - 35℃; for 24h; Irradiation; Sealed tube; Inert atmosphere;

Reference： [1]Ackermann, Lutz; Casnati, Anna; Korvorapun, Korkit; Kuniyil, Rositha; Struwe, Julia; Waeterschoot, Marjo; Zangarelli, Agnese [Angewandte Chemie - International Edition, 2020, vol. 59, # 41, p. 18103 - 18109][Angew. Chem., 2020, vol. 132, # 41, p. 18259 - 18265,7]

44
[ 563-80-4 ]
(4-iodophenyl)hydrazine hydrochloride [ No CAS ]
[ 54136-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In ethanol at 85℃; for 5h;	2.2.2. Synthesis of 5-chloro-2,3,3-trimethyl-3H-indole (6b) General procedure: 4-chlorophenylhydrazine hydrochloride (6a) (4 g, 22.3 mmol) and 3-methyl-2-butanone (2.3 mL, 26.7 mmol) were added to a 100 mLdouble-necked flask. Afterwards, ethanol (25 ml) and sulfuric acid (3 ml,95%) was added. The mixture was refluxed at 85 C for 5 h and wasevaporated in vacuum. The brown solution was washed three times withsaturated NaHCO3 solution and water. The organic layer was dried overNa2SO4 and evaporated. A thick red-brown liquid was the purifiedcompound 6b (3.59 g, 83.02%).

Reference： [1]Liu, Hao; Yin, Juanjuan; Xing, Enyun; Du, Yingying; Su, Yu; Feng, Yaqing; Meng, Shuxian [Dyes and Pigments, 2021, vol. 190]

45
[ 54136-25-3 ]
[ 3720-84-1 ]
5-iodo-2,3,3-trimethyl-1-(3-(triethylammonio)propyl)-3H-indol-1-ium dibromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	In acetonitrile for 48h; Reflux;	5-Iodo-2,3,3-trimethyl-1-(3-(triethylammonio)propyl)-3H-indol-1-ium dibromide (1d): 5-Iodo-2,3,3-trimethyl-3H-indole (1.0g, 3.5mmol) and 3-bromo-N,N,N-triethylpropan-1-aminium bromide (1.23g, 3.9mmol) were stirred in acetonitrile (14mL) at reflux for 2 days. Reaction mixture was diluted with benzene (50mL). In 1h the solvent was decanted and the viscous solid was triturated with diethyl ether, filtered, washed with ether, and dried to yield 1d (0.6g, 29%). 1H NMR (400MHz, DMSO-d6, ppm): δ 8.33 (s, 1H), 8.04 (d, J=7.8Hz, 1H), 7.95 (d, J=7.6Hz, 1H), 4.56 (t, J=7.7Hz, 2H), 3.25 (m, 8H), 2.91 (s, 3H), 2.18 (m, 2H), 1.56 (s, 6H), 1.18 (t, J=7.3Hz, 9H). MS m/z (ESI+) C20H33Br2IN2 calculated [M-2Br]+ 428.17, found m/z 428.20.

Reference： [1]Gellerman, Gary; Kobzev, Dmytro; Kolosova, Olga; Nakonechny, Faina; Patsenker, Leonid; Semenova, Olga; Tatarets, Anatoliy; Yazbak, Fares [Dyes and Pigments, 2021, vol. 195]

46
[ 54136-25-3 ]
C₄₁H₄₃I₂N₂O₂S⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetonitrile / 12 h / 81 °C 2: anhydrous Sodium acetate / ethanol / 4 h / 78 °C 3: N,N-dimethyl-formamide / 18 h / 20 °C

Reference： [1]Chansaenpak, Kantapat; Kamkaew, Anyanee; Lai, Rung-Yi; Noisa, Parinya; Siriwibool, Siriwalee; Sukwattanasinitt, Mongkol; Wangngae, Sirilak; Wet-osot, Sirawit [Bioorganic Chemistry, 2022, vol. 122]

47
[ 54136-25-3 ]
C₆₄H₆₇ClI₂N₅O₄S⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: acetonitrile / 12 h / 81 °C 2.1: anhydrous Sodium acetate / ethanol / 4 h / 78 °C 3.1: N,N-dimethyl-formamide / 18 h / 20 °C 4.1: N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; dmap / dichloromethane / 0.5 h / 0 °C 4.2: 12 h / 30 °C

Reference： [1]Chansaenpak, Kantapat; Kamkaew, Anyanee; Lai, Rung-Yi; Noisa, Parinya; Siriwibool, Siriwalee; Sukwattanasinitt, Mongkol; Wangngae, Sirilak; Wet-osot, Sirawit [Bioorganic Chemistry, 2022, vol. 122]

48
[ 54136-25-3 ]
C₃₄H₃₈ClI₂N₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetonitrile / 12 h / 81 °C 2: anhydrous Sodium acetate / ethanol / 4 h / 78 °C

Reference： [1]Chansaenpak, Kantapat; Kamkaew, Anyanee; Lai, Rung-Yi; Noisa, Parinya; Siriwibool, Siriwalee; Sukwattanasinitt, Mongkol; Wangngae, Sirilak; Wet-osot, Sirawit [Bioorganic Chemistry, 2022, vol. 122]

49
[ 54136-25-3 ]
[ 75-03-6 ]
1-ethyl-5-iodo-2,3,3-trimethyl-3H-indol-1-ium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.9%	In acetonitrile at 81℃; for 12h;	The synthesis of 1-ethyl-5-iodo-2,3,3-trimethyl-3H-indol-1-ium 4.6093 g (16.1657 mmol) of 5-iodo-2,3,3-trimethyl-3H-indole and 10.0854 g (64.6628 mmol) of Iodoethane were dissolved in 15 mL of acetonitrile. The reaction was refluxed at 81 C for 12 h. The mixture was cooled to temperature and the flask was placed in an ice bath. The solid residue was precipitated and collected by filtration, washed with cold acetonitrile to provide white solid product (52.9 %yield). 1H NMR (500 MHz, DMSO-d6): δ 8.31 (s, 1 H, Ar-CH), 8.00 (d, J = 8.5, 1 H, Ar-CH), 7.79 (d, J = 8.5, 1 H, Ar-CH), 4.46 (m, 2 H, N-CH2), 2.81 (s, 3 H, CH3), 1.53 (s, 6 H, CH3), 1.41 (t, J = 7.0, 3 H, CH3). 13C NMR (125 MHz, DMSO-d6): δ 196.7, 144.6, 141.1, 138.1, 132.9, 117.8, 96.7, 54.7, 43.6, 22.2, 14.3, 13.1. HRMS-ESI (m/z): the calculated value (calcd) for C13H17IN+ [M+]: 314.0400, found 314.0404.
52.9%	In acetonitrile at 81℃; for 12h;	The synthesis of 1-ethyl-5-iodo-2,3,3-trimethyl-3H-indol-1-ium 4.6093 g (16.1657 mmol) of 5-iodo-2,3,3-trimethyl-3H-indole and 10.0854 g (64.6628 mmol) of Iodoethane were dissolved in 15 mL of acetonitrile. The reaction was refluxed at 81 C for 12 h. The mixture was cooled to temperature and the flask was placed in an ice bath. The solid residue was precipitated and collected by filtration, washed with cold acetonitrile to provide white solid product (52.9 %yield). 1H NMR (500 MHz, DMSO-d6): δ 8.31 (s, 1 H, Ar-CH), 8.00 (d, J = 8.5, 1 H, Ar-CH), 7.79 (d, J = 8.5, 1 H, Ar-CH), 4.46 (m, 2 H, N-CH2), 2.81 (s, 3 H, CH3), 1.53 (s, 6 H, CH3), 1.41 (t, J = 7.0, 3 H, CH3). 13C NMR (125 MHz, DMSO-d6): δ 196.7, 144.6, 141.1, 138.1, 132.9, 117.8, 96.7, 54.7, 43.6, 22.2, 14.3, 13.1. HRMS-ESI (m/z): the calculated value (calcd) for C13H17IN+ [M+]: 314.0400, found 314.0404.

Reference： [1]Chansaenpak, Kantapat; Kamkaew, Anyanee; Lai, Rung-Yi; Noisa, Parinya; Siriwibool, Siriwalee; Sukwattanasinitt, Mongkol; Wangngae, Sirilak; Wet-osot, Sirawit [Bioorganic Chemistry, 2022, vol. 122]
[2]Chansaenpak, Kantapat; Kamkaew, Anyanee; Lai, Rung-Yi; Noisa, Parinya; Siriwibool, Siriwalee; Sukwattanasinitt, Mongkol; Wangngae, Sirilak; Wet-osot, Sirawit [Bioorganic Chemistry, 2022, vol. 122]

50
[ 54136-25-3 ]
5-iodo-2,3,3-trimethylindoline [ No CAS ]
(S)-5-iodo-2,3,3-trimethylindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89 % ee	With potassium-t-butoxide; hydrogen; C₃₁H₂₈FeMnN₃O₃P⁽¹⁺⁾*Br^(1-) In 1,4-dioxane at 80℃; for 16h; Glovebox; Autoclave; Overall yield = 94 percent; enantioselective reaction;

Reference： [1]Li, Yibiao; Liu, Chenguang; Liu, Qiang; Wang, Mingyang; Xu, Yihan [Angewandte Chemie - International Edition, 2022, vol. 61, # 20][Angew. Chem., 2022, vol. 134, # 20]

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CAS No. :	54136-25-3	MDL No. :	MFCD25964381
Formula :	C₁₁H₁₂IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GCSMQZIBGLQVLL-UHFFFAOYSA-N
M.W :	285.12	Pubchem ID :	21858026
Synonyms :

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
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Prevention
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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Response
Code	Phrase
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P321
P322
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P342	If experiencing respiratory symptoms:
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P353	Rinse skin with water/shower.
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P372	Explosion risk in case of fire.
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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.
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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.
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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.
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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:
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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
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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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
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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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

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