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

HRID 913705Notes

Reaction equation

HRID 913705 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([C:19]([F:22])([F:21])[F:20])[C:13]([C:17]#[N:18])=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH3:23])=[CH:4][CH:3]=1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1>>[CH3:23][C:9]1[N:8]([CH2:7][C:5]2[S:6][C:2]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=3)=[CH:3][CH:4]=2)[C:16]2[C:11]([CH:10]=1)=[C:12]([C:19]([F:22])([F:21])[F:20])[C:13]([C:17]#[N:18])=[CH:14][CH:15]=2

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 67404974HCID 67404974, compound

Product 1

HCID 866206992-Methyl-4-(trifluoromethyl)-1-({5-[3-(trifluoromethyl)phenyl]-2-thienyl}methyl)-1H-indole-5-carbonitrile

Procedure

Synthesized as described in Example 310D using 1-[(5-bromo-2-thienyl)methyl]-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 314B) and [3-(trifluoromethyl)phenyl]boronic acid: 1H NMR (400 MHz, CDCl3) δ 7.67 (s, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.47, (m, 4H), 7.17 (m, 1H), 6.81 (d, J=3.6 Hz, 1H), 6.65 (s, 1H), 5.49 (s, 2H), 2.56 (s, 3H); MS (ES) m/z 463 (M−1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-3afdb28d62fc4854a7966282bd27388f
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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