4-(Trifluoromethyl)phenylboronic acid → 2-[(2R)-4-(3-Chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-5-trifluoromethyl-7-(4-trifluoromethyl-phenyl)-1H-benzoimidazole

HRID 912980Notes

Reaction equation

HRID 912980 reaction equation
Br[C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][C@H:12]3[CH3:24])=[N:10][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:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>>[Cl:23][C:22]1[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]3[NH:8][C:7]4[C:2]([C:34]5[CH:35]=[CH:36][C:31]([C:30]([F:41])([F:40])[F:29])=[CH:32][CH:33]=5)=[CH:3][C:4]([C:25]([F:27])([F:28])[F:26])=[CH:5][C:6]=4[N:10]=3)[C@H:12]([CH3:24])[CH2:13]2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 178461521HCID 178461521, compound

Product 1

HCID 1784615232-[(2R)-4-(3-Chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-5-trifluoromethyl-7-(4-trifluoromethyl-phenyl)-1H-benzoimidazole

Procedure

7-Bromo-2-[(2R)-4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-5-(trifluoromethyl)-1H-benzoimidazole (95 mg, 0.2 mmol, Example 77) and 4-(trifluoromethyl)phenylboronic acid (47 mg, 0.25 mmol, Aldrich) reacted under the conditions of Example 51a to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 515 (M+1).

Sources & evidence

ORD record
ord-a002c45edc5041e3a68276e66e2fbfee
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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