Toluene → 1-Benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indole

HRID 1791423Notes

Reaction equation

HRID 1791423 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 2857561-Benzyl-5-Bromo-1H-IndoleHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 220329501-Benzyl-5-[4-(trifluoromethyl)phenyl]-1H-indoleYield 12%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Following the procedure described in Step 2 of Example 5 1-benzyl-5-bromo-1H-indole (2.22 g , 7.76 mmol) was coupled to 4-trifluoromethylphenyl boronic acid (1.62 g, 8.54 mmol), using tetrakis(triphenylphosphine)palladium (0.892 g, 0.772 mmol), and potassium carbonate (4.29 g, 31.1 mmol) in water (17 mL), ethanol (4 mL), and toluene (37 mL). Purification by flash chromatography using 0.5-1.0% ethyl acetate in hexane as eluant afforded the title compound as a light yellow solid (0.317 g, 12%). 1HNMR (200 MHz, DMSO-d6): δ 7.7-8.0 (m, 5H), 7.4-7.6 (m, 3H), 7.15-7.4 (m, 5H), 6.6 (d, 1H, J=3.6 Hz), and 5.45 ppm (s, 2H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2634fc9878574c259590b03776e602df
Source dataset
uspto-grants-2006_07
Patent number
US07074817B2

Reaction notes

Loading…