3,4-Difluorobenzeneboronic acid → 5-(3,4-Difluoro-phenyl)-6-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole

HRID 730810Notes

Reaction equation

HRID 730810 reaction equation
Br[C:2]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][C:5]2[NH:6][C:7]([N:9]3[CH2:14][CH2:13][N:12]([C:15]4[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[F:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38]>>[F:31][C:32]1[CH:33]=[C:34]([C:2]2[C:26]([C:27]([F:28])([F:29])[F:30])=[CH:25][C:5]3[NH:6][C:7]([N:9]4[CH2:10][CH2:11][N:12]([C:15]5[C:20]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:18]=[CH:17][N:16]=5)[CH2:13][CH2:14]4)=[N:8][C:4]=3[CH:3]=2)[CH:35]=[CH:36][C:37]=1[F:38]

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 115115725-Bromo-6-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole

Product 1

HCID 578351465-(3,4-Difluoro-phenyl)-6-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole

Procedure

The reaction of 5-bromo-6-trifluoromethyl-2-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-1H-benzoimidazole (250 mg, 0.5 mmol, Example 89g) with 3,4-difluorophenylboronic acid (95 mg, 0.60 mmol, Aldrich) under the conditions of Example 88 afforded the title compound as a white solid. MS (ESI, pos. ion) m/z: 528.0 (M+1).

Sources & evidence

ORD record
ord-88f495990dd945c4b5bd68ba21959ede
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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