3-(Trifluoromethyl)phenylboronic acid → 2-[4-(3,5-Dichloropyridin-2-yl)piperazin-1-yl]-5-(trifluoromethyl)-7-[3-(trifluoromethyl)phenyl]-1H-benzoimidazole

HRID 912809Notes

Reaction equation

HRID 912809 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([Cl:23])=[CH:21][C:20]([Cl:24])=[CH:19][N:18]=4)[CH2:13][CH2:12]3)[NH:7][C:6]=2[CH:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>>[Cl:23][C:22]1[C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:8]3[NH:9][C:10]4[C:2]([C:35]5[CH:34]=[CH:33][CH:32]=[C:31]([C:30]([F:41])([F:40])[F:29])[CH:36]=5)=[CH:3][C:4]([C:25]([F:27])([F:26])[F:28])=[CH:5][C:6]=4[N:7]=3)[CH2:16][CH2:15]2)=[N:18][CH:19]=[C:20]([Cl:24])[CH:21]=1

Participants

3

Reactant 2

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 578350764-Bromo-2-[4-(3,5-dichloropyridin-2-yl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole

Product 1

HCID 1785061442-[4-(3,5-Dichloropyridin-2-yl)piperazin-1-yl]-5-(trifluoromethyl)-7-[3-(trifluoromethyl)phenyl]-1H-benzoimidazole

Procedure

The reaction of 4-bromo-2-[4-(3,5-dichloropyridin-2-yl)piperazin-1-yl]-6-trifluoromethyl-1H-benzoimidazole (99 mg, 0.2 mmol, Example 9) and 3-trifluoromethylphenylboronic acid (48 mg, 0.25 mmol, Aldrich) under the conditions of Example 10 gave the title compound as a light-yellow amorphous solid. MS (ESI, pos. ion) m/z: 560 (M+1).

Sources & evidence

ORD record
ord-9cb9bafb60a548ee9a0e2adb7aabdfe3
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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