Sodium Carbonate → 1-Benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indole

HRID 2221190Notes

Reaction equation

HRID 2221190 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[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-].[Na+].[Na+]>O.C(O)C.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([F:30])([F:29])[F:18])=[CH:21][CH:22]=3)[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 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 220329571-benzyl-6-bromo-1H-indole

Product 1

HCID 220329201-Benzyl-6-[4-(trifluoromethyl)phenyl]-1H-indoleYield 71%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Following the procedure described in Step 2 of Example 5, 1-benzyl-6-bromo-1H-indole (0.490 g, 1.71 mmol), was coupled to 4-trifluoromethylbenzeneboronic acid (0.376 g, 1.98 mmol), using tetrakis(triphenylphosphine) palladium (0.0663 g, 0.057 mmol) and sodium carbonate (0.733 g, 6.92 mmol) in water (3.5 mL), ethanol (2 mL) and toluene (10 mL). Purification by flash chromatography using 0-1% ethyl acetate in hexane as an eluant yielded the title compound as a yellow solid (0.426 g, 71%), mp: 83-85° C. 1HNMR (300 MHz, DMSO-d6): δ 7.9 (d, 3H, J=7.7 Hz), 7.8 (d, 2H, J=7.7 Hz), 7.7 (d, 1H, J=7.7 Hz), 7.6 (d, 1H, J=3.9 Hz), 7.4 (d, 1H, J=7.7 Hz), 7.2-7.4 (m, 5H), 6.55 (d, 1H, J=2.3 Hz), and 5.55 ppm (s, 2H).

Workup

  1. customPurification by flash chromatography

Sources & evidence

ORD record
ord-af95791bbc8642d18bf5b37417b30de1
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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