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

HRID 912978Notes

Reaction equation

HRID 912978 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]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=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:33]=[CH:32][CH:31]=[C:30]([F:29])[CH:35]=5)=[CH:3][C:4]([C:25]([F:28])([F:26])[F:27])=[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 27339863-Fluorophenylboronic acidHCID 178461521HCID 178461521, compound

Product 1

HCID 1784615222-[(2R)-4-(3-Chloro-pyridin-2-yl)-2-methyl-piperazin-1-yl]-7-(3-fluoro-phenyl)-5-trifluoromethyl-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 3-fluoro-phenylboronic acid (35 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: 490 (M+1).

Sources & evidence

ORD record
ord-28792d15a8a34fc29328a01eb1d85865
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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