[ CAS No. 948-65-2 ] {[proInfo.proName]}

Name: 948-65-2|2-Phenyl-1H-indole|98%
Brand: Ambeed
SKU: A190721
Price: 5.0 USD
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Quality Control of [ 948-65-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 948-65-2 ]

SDS Specification

Alternatived Products of [ 948-65-2 ]

Product Details of [ 948-65-2 ]

CAS No. :	948-65-2	MDL No. :	MFCD00005608
Formula :	C₁₄H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KLLLJCACIRKBDT-UHFFFAOYSA-N
M.W :	193.24	Pubchem ID :	13698
Synonyms :

Calculated chemistry of [ 948-65-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.73
TPSA :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.2
Log Po/w (XLOGP3) :	-0.54
Log Po/w (WLOGP) :	3.83
Log Po/w (MLOGP) :	3.06
Log Po/w (SILICOS-IT) :	4.16
Consensus Log Po/w :	2.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.37
Solubility :	8.21 mg/ml ; 0.0425 mol/l
Class :	Very soluble
Log S (Ali) :	0.68
Solubility :	920.0 mg/ml ; 4.76 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-5.8
Solubility :	0.000304 mg/ml ; 0.00000157 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 948-65-2 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H318-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 948-65-2 ]

* 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.

Downstream synthetic route of [ 948-65-2 ]

[ 948-65-2 ] Synthesis Path-Downstream 1~88

1
[ 50-00-0 ]
[ 948-65-2 ]
[ 4662-03-7 ]

Reference： [1]Patent: US2222344,1939,
[2]Patent: DE679283,1937,
DRP/DRBP Org.Chem.,

2
[ 948-65-2 ]
[ 13338-49-3 ]
[ 101721-05-5 ]

Reference： [1]Patent: US2751393,1954,
[2]Patent: DE1004617,1954,

3
[ 948-65-2 ]
[ 2050-85-3 ]
[ 123613-05-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1989,p. 200 - 201

4
[ 948-65-2 ]
[ 51114-68-2 ]
[ 106111-62-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1986,p. 607 - 610

5
[ 948-65-2 ]
[ 7722-84-1 ]
[ 64-19-7 ]
[ 579-93-1 ]

Reference： [1]Chemische Berichte,1955,vol. 88,p. 1066,1070

6
[ 948-65-2 ]
[ 10028-15-6 ]
[ 141-78-6 ]
[ 579-93-1 ]
[ 1022-46-4 ]
[ 33768-43-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1950,p. 555,560

7
[ 948-65-2 ]
[ 50606-58-1 ]
[ 244086-73-5 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 1603 - 1614

8
[ 108-86-1 ]
[ 143360-89-8 ]
[ 948-65-2 ]
[ 3469-20-3 ]
[ 2415-33-0 ]

Reference： [1]Synthesis,2003,p. 728 - 734

9
[ 17763-67-6 ]
[ 143360-89-8 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Synthesis,2003,p. 728 - 734

10
[ 557785-76-9 ]
[ 948-65-2 ]
[ 2538-52-5 ]
[ 3558-69-8 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2002,vol. 38,p. 1190 - 1199

11
[ 108-86-1 ]
[ 143360-89-8 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3271 - 3274

12
[ 108-86-1 ]
[ 125345-25-7 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3271 - 3274

13
[ 5391-39-9 ]
[ 948-65-2 ]
2-phenyl-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole hydrochloride [ No CAS ]

Reference： [1]Patent: EP1266897,2002,A2 .Location in patent: Page 49

14
[ 948-65-2 ]
[ 79-37-8 ]
[ 925-90-6 ]
[ 78190-11-1 ]
[ 256446-54-5 ]

Yield	Reaction Conditions	Operation in experiment
15.6 g (35.6 mmol; 63%)	With ammonium chloride;SiO2; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;	A. 3-(2-Phenyl-1H-indole-3-carbonyl)piperidine-1-carboxylic acid benzyl ester A solution of 14.8 g (56.3 mmol) of N-benzyloxycarbonylnipecotic acid in anhydrous dichloromethane (100 ml) under an atmosphere of nitrogen was treated with oxalyl chloride (7.4 ml, 84.4 mmol) followed by 2 drops of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 90 min at which time the dichloromethane was evaporated in vacuo. The residue was dissolved in anhydrous toluene (75 ml) and the resulting solution evaporated in vacuo. The residue was dissolved in anhydrous benzene (50 ml) to give Solution A. A solution of 21.7 g (113 mmol) of 2-phenylindole in anhydrous benzene (250 ml) under an atmosphere of nitrogen was added using a cannula to a solution of ethylmagnesium bromide (37.5 ml of a 3M solution in diethyl ether, 113 mmol) and the resulting mixture stirred at room temperature for 15 min to give Solution B. Solution A was added in one portion to rapidly stirred solution B and the resulting mixture stirred at room temperature for 30 min. The reaction was quenched by the addition of saturated ammonium chloride solution (200 ml). The organic layer was separated, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 10% EtOAc in hexanes then 20% EtOAc in hexanes) to afford 15.6 g (35.6 mmol; 63%) of 3-(2-phenyl-1H-indole-3-carbonyl)piperidine-1-carboxylic acid benzyl ester as a clear oil. deltaH (360 MHz; CDCl3) 0.91-1.07 (1H, m, aliphatic), 1.50-1.65 (2H, m, aliphatics), 1.88-1.96 (1H, m, aliphatic), 2.58-2.82 (2H, m, aliphatics), 2.86-3.08 (1H, m, aliphatic), 3.92-4.06 (1H, m, aliphatic), 4.08-4.17 (1H, m, aliphatic), 5.05 (2H, d, J 3.8, PhCH2), 7.24-7.52 (13H, m, aromatics), 8.24-8.30 (1H, m, aromatic), 8.75 (1H, br s, NH); m/z (ES+) 439 (M++H, 100%).

Reference： [1]Patent: US6479480,2002,B1

15
[ 948-65-2 ]
[ 40064-34-4 ]
[ 221109-25-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With phosphoric acid; In acetic acid; ethyl acetate;	Step 1 3-(1,2,3,6-Tetrahydropyridin-4-yl)-2-phenyl-1H-indole 2-Phenylindole (25 g, 130 mmol) was stirred at 80 C. in AcOH (200 ml), and <strong>[40064-34-4]4-piperidone hydrochloride hydrate</strong> (50 g, 376 mmol) and 1M phosphoric acid (100 ml) added. After a further 6 h, the mixture was poured into ice/ammonia, and extracted with EtOAc (3*200 ml). The combined organic layers were washed with water and brine, dried, and evaporated in vacuo to give a pale yellow solid. This was suspended in boiling EtOAc (200 ml), cooled to room temperature overnight, and the solid collected, washed with EtOAc and dried to give the title compound (26 g, 73%) as a pale yellow solid; deltaH (360 MHz, d6-DMSO) 2.00-2.10 (2H, m, NCH2CH2), 2.89 (2H, t, J 5, NCH2CH2), 3.40-3.45 (2H, m, NCH2CH), 5.78 (1H, br s, NCH2CH), 7.00 (1H, t, J 7, indole-H), 7.08 (1H, t, J 7, indole-H), 7.20-7.50 (5H, m, ArH), 7.69 (2H, d, J 7, ArH), 11.3 (1H, br s, indole NH); m/z (ES+) 275 (M++H).

Reference： [1]Patent: US6316468,2001,B1

16
[ 108-86-1 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2929 - 2936
[2]Tetrahedron Letters,2008,vol. 49,p. 2499 - 2502

17
[ 851670-79-6 ]
[ 260-94-6 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 837 - 843

18
[ 1075651-51-2 ]
[ 260-94-6 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 837 - 843

19
[ 948-65-2 ]
[ 3195-78-6 ]
[ 59959-19-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 273 - 277

20
[ 1122-10-7 ]
[ 948-65-2 ]
3-bromo-4-(2-phenyl-1<i>H</i>-indol-3-yl)-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Physical Chemistry Chemical Physics,2010,vol. 12,p. 9783 - 9793

21
[ 78385-26-9 ]
[ 948-65-2 ]
[ 1069473-27-3 ]

Reference： [1]Dyes and Pigments,2011,vol. 91,p. 177 - 181

22
[ 78385-26-9 ]
[ 948-65-2 ]
[ 1314235-54-5 ]

Reference： [1]Dyes and Pigments,2011,vol. 91,p. 177 - 181

23
[ 948-65-2 ]
[ 62005-48-5 ]
N-<2-(2-phenylindol-3-yl)ethyl>acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6351 - 6357

24
[ 948-65-2 ]
[ 20069-09-4 ]
[ 1337905-58-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With iodine; at 80℃; for 24h;	General procedure: To a mixture of piplartine (1 mmol) and Indole (3 mmol), Iodine (10 mol %) was added. The contents were refluxed in dichloroethane (5 mL) for an appropriate time (12-48 h) and reaction was monitored by thin-layer chromatography (TLC). After complete conversion, the solvent was evaporated, and the product was washed with hypo solution (10 mL), and then extracted with chloroform. The combined organic layers was dried over anhydrous sodium sulphate and evaporated under reduced pressure, purified by silica-gel column chromatography to afford pure product mono-adduct (2a-2k) and di-adduct (3a-3k).
	With iodine; In 1,2-dichloro-ethane; for 30h;Reflux;	Experimental Procedure for (3e); To a mixture of piplartine (0.317 g, 1 mmol) and 2-phenylindole (0.579 g, 3 mmol), Iodine (0.0152 g, 12 mol %) was added. The contents were refluxed in 1,2-dichloroethane (5 ml) for an appropriate time (30 h). The reaction was monitored by thin-layer chromatography (TLC). After complete conversion, the solvent was evaporated, and the product was washed with saturated hypo solution (10 ml), and then extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulphate and evaporated using rotary evaporator, purified by silica-gel (60-120 mesh) column chromatography by Ethylacetate:Hexane (3:7) to afford pure di adduct (3e). Compound 2e (mono adduct) was not observed in this reaction.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 344 - 361
[2]Patent: US2012/245357,2012,A1 .Location in patent: Page/Page column 9

25
[ 948-65-2 ]
[ 4662-03-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8152 - 8163

26
[ 948-65-2 ]
[ 104-15-4 ]
[ 144657-66-9 ]
[ 1443528-02-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3539 - 3544

27
[ 5378-52-9 ]
[ 932-87-6 ]
[ 948-65-2 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 6807 - 6812

28
[ 108-86-1 ]
[ 2727-71-1 ]
[ 536-74-3 ]
[ 948-65-2 ]
[ 3469-20-3 ]
[ 143360-89-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 4558 - 4562
[2]Journal of Organic Chemistry,2013,vol. 78,p. 4558 - 4562
[3]Journal of Organic Chemistry,2013,vol. 78,p. 4558 - 4562

29
[ 108-86-1 ]
[ 2727-71-1 ]
[ 536-74-3 ]
[ 948-65-2 ]
[ 3469-20-3 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 4558 - 4562

30
[ 29927-08-0 ]
[ 948-65-2 ]
2-phenyl-3-(5,6-dimethylbenzothiazol-2-yldiazenyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: 2-Aminobenzothiazole (0.30 g, 2.0 mmol) was dissolved in hot glacial acetic acid/propionic acid mixture (2:1, 6.0 ml) and was rapidly cooled in an ice-salt bath to -5 C. The mixture was then stirred for 2 h. at 0-5 C. The liquor was then added in portions during 30 min to a cold solution of nitrosyl sulfuric acid [prepared from sodium nitrite (0.15 g) and concentrated sulfuric acid (3 ml at 50 C)]. The mixture was stirred for an additional 2 h at 0 C. Excess nitrous acid was destroyed by the addition of urea. The resulting diazonium salt was cooled in salt/ice mixture. 2-methlyindole(0.26 g, 2.0 mmol) was dissolved in mixture of acetic acid/propionic acid solution (3:1, 8.0 ml) and cooled in salt/ice bath and then cold diazonium solution was added to this cooled solution by stirring in a dropwise manner. The solution was stirred at 0-5 C for 2 h. and pH of the reaction mixture was maintained at 4-6 by simultaneous addition of saturated sodium carbonate solution.The mixture was stirred for a further 1 h at 5 C. The resulting product was filtered, washed with water, dried and crystallized from ethanol mixture gave brown powder (yield: 0.29 g, 51%; m.p: 168-170 C), FT-IR (KBr) numax: 3345 (indole -NH), 3059 (aromatic C-H), 2969, 2920 (aliphatic C-H), 1605 (C=C) cm-1; 1HNMR (DMSO-d6/CDCl3): d 9.71 (b, indole -NH), 7.98 (1H,m), 7.37(1H,m), 7.30-7.15 (4H,m), 6.82 (2H,m), 2.36 (3H,s).Anal. Calcd. For C16H12N4S: C, 65.73; H, 4.14; N, 19.16; S, 10.97Found: C, 65.68; H, 4.19; N, 19.11; S, 10.92%.MS (m/z, 70 eV): 292.0 (M+), 277.0, 158.0, 130.0.

Reference： [1]Journal of Molecular Structure,2013,vol. 1047,p. 22 - 30

31
[ 948-65-2 ]
[ 57310-39-1 ]
2-methylindolo[1,2-f]phenanthridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 7966 - 7977

32
[ 948-65-2 ]
[ 97-08-5 ]
3-(4-chloro-3-nitrophenylsulfinyl)-2-phenyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With zinc(II) oxide; In neat (no solvent); at 80℃; for 3h;	General procedure: Indole (8.54 mmol), phenylsulfonyl chloride (10.25 mmol) and oxide fine powder (25.62 mmol) were blended and the mixture was stirred for the period indicated (TLC) at 80 C. After reaction, the crude mixture was washed with acetone or dichloromethane and filtered through celite. The concentrated filtrate was flash chromatographied (hexane/ethyl acetate 3/1, 5/1 or 1/3) on silica gel, obtaining the desired product. When indoles 1a, 1b, 1j and 1l andsulfonyl chlorides 2f, 2h, 2j, 2k were used, the correspondent 2- or 3-sulfinylindole 6 or 7 was also isolated.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 6237 - 6241

33
[ 948-65-2 ]
[ 579-93-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With oxygen; copper(l) cyanide; sodium carbonate; In dimethyl sulfoxide; at 80℃; under 760.051 Torr; for 24h;Catalytic behavior;	A mixture of 1a(0.20 mmol), CuCl (4.0 mg, 0.04 mmol) and Na2CO3 (42mg, 0.40 mmol) in DMSO (1.0 mL) was stirred at 80 C under an oxygen atmosphere (1 atm).After 24 h, the mixture was quenched with 10% HCl at 0 C and extracted withEtOAc. The organic extracts were washed with H2O and brine, dried over Na2SO4, and then concentrated. The residue was dissolved in saturated NaHCO3, washed withCH2Cl2 and the aqueous fraction was acidified withdrop-wise addition of 10% HCl at 0 C and extracted with ethyl acetate. The organic extracts were washed with H2Oand brine, dried over Na2SO4, and then concentrated

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2991 - 2993
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5962 - 5970

34
[ 948-65-2 ]
[ 71999-74-1 ]
[ 1610423-36-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 3567 - 3571

35
[ 948-65-2 ]
[ 62005-48-5 ]
[ 1629189-13-4 ]

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

36
[ 221044-05-9 ]
[ 6843-66-9 ]
[ 948-65-2 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2614 - 2617

37
[ 948-65-2 ]
[ 20651-67-6 ]
1-(4-butylphenyl)-2-phenyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 24h;Inert atmosphere;	General procedure: A 10 mL Schlenk tube was charged with 2-phenylindole 1a (193.2 mg, 1.0 mmol), CuI (10 mol%, 19.0 mg, 0.1 mmol) and K3PO4 (424 mg, 2.0 mmol). The Schlenk tube was evacuated and filled with N2 (this procedure was repeated three times), and then toluene (2.0 mL), DMEDA (20 mol%, 17.6 mg, 0.2 mmol) and iodobenzene 2a (244.8 mg, 1.2 mmol) were added. The resulting mixture was stirred at 110 C for 24 h. After cooling to room temperature, the reaction mixture was quenched and extracted with ethyl acetate (10 mL × 3). The organic extracts were combined, dried over Na2SO4 and concentrated under reduced pressure, and then purified by silica gel chromatograph (petroleum ether) to yield the desired product as a white solid (245.1 mg, 91% yield). The data of compounds 3a-q can be found in Supporting information.

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 1240 - 1243

38
[ 948-65-2 ]
[ 1885-35-4 ]
[ 1416576-34-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With trifluorormethanesulfonic acid; palladium diacetate; acetic acid; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine; In 1,4-dioxane; water; at 100℃; for 24h;	General procedure: To a mixture of indole (1 mmol), nitrile (1.2 mmol), Pd(OAc)2 (5 mol%), L1 (5mol%), dioxane (1 mL), acetic acid (0.6 mL) and H2O (0.4 mL) were added and stirred at100 C for 24 h. The reaction mixture was neutralized with saturated NaHCO3 solution andthen extracted with ethyl acetate. The organic phase was dried over Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by flash columnchromatography on a silica gel using petroleum ether/EtOAc as the eluent to give the desiredproduct.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 7198 - 7202

39
[ 101-42-8 ]
[ 948-65-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 672 - 675
[2]Organic Letters,2015,vol. 17,p. 672 - 675

40
[ 948-65-2 ]
[ 142-26-7 ]
N-<2-(2-phenylindol-3-yl)ethyl>acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 3217 - 3222

41
[ 948-65-2 ]
[ 68-12-2 ]
[ 2274-42-2 ]
[ 1519005-29-8 ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: To a stirred solution of the suitable indole 11-17 (10 mmol) in dry DMF (5 mL), benzoyl chloride (1.41 g, 10 mmol) was added in a single portion. After stirring at rt for 1 h, the reaction mixture was allowed to stand at 0 C for 18-48 h. Then, a solution of the suitable active methylene reagent (11 mmol) and triethylamine (1.21 g, 12 mmol) in dry DMF (8 mL) pre-warmed at 80 C, were added in a single portion. The reaction mixture was stirred for 45 min at 90 C (for 5b and 5u: 1.5 h at 105 C; for 5v: 1.5 h at 120 C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50 mL). Then, work-ups 1-4 were carried out, as follows: Work-up 1 (for 2a, c-g, 3b, 4a, b, 5a-h, j, l-p, r, s, u, x, z, 6a, b, 7a, b, 8a, b): the precipitate obtained was filtered off, dried and crystallized from the suitable solvent or solvent mixture. Work-up 2 (for 4d, 5i, w, y): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3 * 20 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. Work-up 3 (for 4c, 5k, q, t): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from the suitable solvent or solvent mixture. Work-up 4 (for 2b, 3a, 5v, aa-ac): the reaction mixture was extracted with ethyl acetate (2b, 3a, 5ac) or CH2Cl2 (5v, aa, ab) (3 * 35 mL). The combined organic extracts were washed with water (5 * 30 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 3a and 5v, ac were crystallized from the proper solvent(s). Conversely, the crude products of 2b and 5z, aa were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 648 - 660

42
[ 948-65-2 ]
[ 68-12-2 ]
[ 2881-63-2 ]
ethyl (E)-2-(4-chlorobenzoyl)-3-(2-phenyl-1H-indol-3-yl)prop-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		General procedure: To a stirred solution of the suitable indole 11-17 (10 mmol) in dry DMF (5 mL), benzoyl chloride (1.41 g, 10 mmol) was added in a single portion. After stirring at rt for 1 h, the reaction mixture was allowed to stand at 0 C for 18-48 h. Then, a solution of the suitable active methylene reagent (11 mmol) and triethylamine (1.21 g, 12 mmol) in dry DMF (8 mL) pre-warmed at 80 C, were added in a single portion. The reaction mixture was stirred for 45 min at 90 C (for 5b and 5u: 1.5 h at 105 C; for 5v: 1.5 h at 120 C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50 mL). Then, work-ups 1-4 were carried out, as follows: Work-up 1 (for 2a, c-g, 3b, 4a, b, 5a-h, j, l-p, r, s, u, x, z, 6a, b, 7a, b, 8a, b): the precipitate obtained was filtered off, dried and crystallized from the suitable solvent or solvent mixture. Work-up 2 (for 4d, 5i, w, y): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3 * 20 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. Work-up 3 (for 4c, 5k, q, t): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from the suitable solvent or solvent mixture. Work-up 4 (for 2b, 3a, 5v, aa-ac): the reaction mixture was extracted with ethyl acetate (2b, 3a, 5ac) or CH2Cl2 (5v, aa, ab) (3 * 35 mL). The combined organic extracts were washed with water (5 * 30 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 3a and 5v, ac were crystallized from the proper solvent(s). Conversely, the crude products of 2b and 5z, aa were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 648 - 660

43
[ 948-65-2 ]
[ 62020-09-1 ]
[ 68-12-2 ]
methyl (2E)-2-(methylsulfonyl)-3-(2-phenyl-1H-indol-3-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		General procedure: To a stirred solution of the suitable indole 11-17 (10 mmol) in dry DMF (5 mL), benzoyl chloride (1.41 g, 10 mmol) was added in a single portion. After stirring at rt for 1 h, the reaction mixture was allowed to stand at 0 C for 18-48 h. Then, a solution of the suitable active methylene reagent (11 mmol) and triethylamine (1.21 g, 12 mmol) in dry DMF (8 mL) pre-warmed at 80 C, were added in a single portion. The reaction mixture was stirred for 45 min at 90 C (for 5b and 5u: 1.5 h at 105 C; for 5v: 1.5 h at 120 C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50 mL). Then, work-ups 1-4 were carried out, as follows: Work-up 1 (for 2a, c-g, 3b, 4a, b, 5a-h, j, l-p, r, s, u, x, z, 6a, b, 7a, b, 8a, b): the precipitate obtained was filtered off, dried and crystallized from the suitable solvent or solvent mixture. Work-up 2 (for 4d, 5i, w, y): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3 * 20 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. Work-up 3 (for 4c, 5k, q, t): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from the suitable solvent or solvent mixture. Work-up 4 (for 2b, 3a, 5v, aa-ac): the reaction mixture was extracted with ethyl acetate (2b, 3a, 5ac) or CH2Cl2 (5v, aa, ab) (3 * 35 mL). The combined organic extracts were washed with water (5 * 30 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 3a and 5v, ac were crystallized from the proper solvent(s). Conversely, the crude products of 2b and 5z, aa were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 648 - 660

44
[ 948-65-2 ]
[ 34097-60-4 ]
[ 68-12-2 ]
[ 1519005-38-9 ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: To a stirred solution of the suitable indole 11-17 (10 mmol) in dry DMF (5 mL), benzoyl chloride (1.41 g, 10 mmol) was added in a single portion. After stirring at rt for 1 h, the reaction mixture was allowed to stand at 0 C for 18-48 h. Then, a solution of the suitable active methylene reagent (11 mmol) and triethylamine (1.21 g, 12 mmol) in dry DMF (8 mL) pre-warmed at 80 C, were added in a single portion. The reaction mixture was stirred for 45 min at 90 C (for 5b and 5u: 1.5 h at 105 C; for 5v: 1.5 h at 120 C). After cooling to rt, Et3N·HCl precipitated and the resulting suspension was treated with water (50 mL). Then, work-ups 1-4 were carried out, as follows: Work-up 1 (for 2a, c-g, 3b, 4a, b, 5a-h, j, l-p, r, s, u, x, z, 6a, b, 7a, b, 8a, b): the precipitate obtained was filtered off, dried and crystallized from the suitable solvent or solvent mixture. Work-up 2 (for 4d, 5i, w, y): the precipitate was filtered off and dissolved in CH2Cl2. The organic layer was washed with water (3 * 20 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the solvent, the crude product was purified by crystallization from ethanol. Work-up 3 (for 4c, 5k, q, t): the precipitate was filtered off, air dried, purified by chromatography (eluents: petroleum ether/ethyl acetate) and then crystallized from the suitable solvent or solvent mixture. Work-up 4 (for 2b, 3a, 5v, aa-ac): the reaction mixture was extracted with ethyl acetate (2b, 3a, 5ac) or CH2Cl2 (5v, aa, ab) (3 * 35 mL). The combined organic extracts were washed with water (5 * 30 mL), dried over anhydrous Na2SO4 and filtered through a pad of Florisil. After evaporation of the filtrate, the crude products 3a and 5v, ac were crystallized from the proper solvent(s). Conversely, the crude products of 2b and 5z, aa were purified by chromatography (eluent: petroleum ether/ethyl acetate) and then crystallized from the proper solvent mix.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 648 - 660

45
[ 948-65-2 ]
[ 80-17-1 ]
[ 3469-20-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2824 - 2827

46
[ 948-65-2 ]
[ 31608-22-7 ]
C₂₃H₂₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.9%		Compound 3 (5.8g, 30mmol) and cooled with a mixture of ice bath N, N- dimethylformamide (50ml), 60% sodium hydride (1.57 g, 36 mmol) and the mixture was stirred for 10 minutes. Compound 8 (6.5ml, 36mmol) was added dropwise, and stirred for 30 minutes. The mixture was stirred for 1 hour while returning to room temperature. In a hot bath 45C , the mixture was heated with stirring for 2 hours. Ice-cooled and water was added, extracted with toluene, washed twice and the organic layers with saturated brine. And concentrated under reduced pressure and dried with anhydrous sodium sulfate. Silica gel column chromatography - (hexane / chloroform = 3/1 1/1) to obtain Compound 9 (2.19g, 20.9% yield) as a pale yellow oil.

Reference： [1]Patent: JP5772122,2015,B2 .Location in patent: Paragraph 0187; 0188

47
[ 25711-25-5 ]
[ 948-65-2 ]
benzyl (2-(2-phenyl-1H-indol-3-yl)ethyl)carbamate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 6095 - 6110

48
[ 948-65-2 ]
[ 1835-49-0 ]
C₆₄H₄₈N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		2.40 g (60.0 mmol) of 60% sodium hydride was placed in a 200-mE three-neck flask, the interior of the flask was substituted with nitrogen, and 100 mE of tetrahydrofuran was added thereto, followed by stirring. 9.65 g (50.0 mmol) of 2-phenyl-1H-indole was added to the mixture, which was stirred under a nitrogen stream at room temperature for 30 minutes. 2.00 g (10.0 mmol) of <strong>[1835-49-0]tetrafluoroterephthalonitrile</strong> was added to the mixture, and the mixture was stirred under a nitrogen atmonphere at room temperature for 24 hours. After stirring, approximately 50 mE of water was gradually added to the mixture, followed by stirring. After stirring, an organic layer and an aqueous layer were separated, and the aqueous layer was extracted with toluene. The organic layer and the extracted solution were combined to each other and rinsed with a saturated sodium chloride aqueous solution. After rinsing, the organic layer was dried by adding magnesium sulfate thereto. Afier drying, the mixture was suction-filtered to provide a filtrate. The resulting filtrate was concentrated to provide a solid matter, which was dissolved in chloroform, and the solution was suction-filtered through Celite and silica gel to provide a filtrate. The resulting filtrate was concentrated to provide a solid matter, which was rinsed with isopropanol. Afier rinsing, the solid matter was rinsed with ethyl acetate, thereby providing an orange powdered solid matter in a yield amount of 1.70 g and a yield of 19.0%.

Reference： [1]Patent: US9502668,2016,B2 .Location in patent: Page/Page column 135; 136

49
[ 948-65-2 ]
[ 16308-68-2 ]
1-allyl-6-methylindolo[2,1-a]isoquinoline [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2258 - 2261

50
[ 2973-50-4 ]
potassium phenyltrifluoborate [ No CAS ]
[ 948-65-2 ]

Yield	Reaction Conditions	Operation in experiment
92.8%	With 4,4'-dimethyl-2,2'-bipyridines; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In water; at 70℃; for 40h;Inert atmosphere;	To a suitable amount of water at room temperature was added 100 mmol of the compound of the above formula (I), 150 mmol of the compound of the above formula (II)15 mmol of palladium acetylacetonate (Pd (acac) 2), 10 mmol of nitrogen-containing ligand L1 and 1000 mmol of acid promoter p-toluenesulfonic acid monohydrate were charged and then purged with nitrogen to maintain the reaction atmosphere in an inert atmosphere; ,And the reaction was stirred at this temperature for 40 hours; After the reaction,The mixture was poured into ethyl acetate, washed sequentially with saturated aqueous NaHCO3 and brine, the aqueous layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined (ie, the combined organic and extracted organic layers were combined) , Dried over anhydrous Na2SO4,The solvent was distilled off under reduced pressure and the residue was purified by flash column chromatography (petroleum ether / ethyl acetate, both of a volume ratio of 8: 1) to give the compound of the above formula (III) as a white solid in 92.8% yield.

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4300 - 4307
[2]Patent: CN106957253,2017,A .Location in patent: Paragraph 0046; 0047; 0048; 0049

51
[ 948-65-2 ]
[ 18637-00-8 ]
(1Z,3Z)-4-(2-ethoxyphenyl)-2-phenylbenzo[f][1,3,5]triazocin-6(5H)-one [ No CAS ]