3-(Trifluoromethyl)phenylboronic acid → 2-Methyl-4-(trifluoromethyl)-1-{[3'-(trifluoromethyl)-3-biphenylyl]methyl}-1H-indole-5-carbonitrile

HRID 2102143Notes

Reaction equation

HRID 2102143 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([C:20]([F:23])([F:22])[F:21])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=3)[CH:11]=[C:10]2[CH3:24])[CH:5]=[CH:6][CH:7]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>>[CH3:24][C:10]1[N:9]([CH2:8][C:4]2[CH:3]=[C:2]([C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=3)[CH:7]=[CH:6][CH:5]=2)[C:17]2[C:12]([CH:11]=1)=[C:13]([C:20]([F:23])([F:22])[F:21])[C:14]([C:18]#[N:19])=[CH:15][CH:16]=2

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 674050351-[(3-Bromophenyl)methyl]-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 866207022-Methyl-4-(trifluoromethyl)-1-{[3'-(trifluoromethyl)-3-biphenylyl]methyl}-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 310D using 1-[(3-bromophenyl)methyl]-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 318A) and [3-(trifluoromethyl)phenyl]boronic acid: 1H NMR (400 MHz, CDCl3) δ 7.73 (s, 1H), 7.65-7.35 (m, 8H), 6.81 (d, J=7.6 Hz, 1H), 6.68 (s, 1H), 5.44 (s, 2H), 2.48 (s, 3H): MS (ES) m/z 459 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-d9728d77bd6644d0b5bbf6ba57c4de09
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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