1-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid → 6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-(4-trifluoromethyl-phenyl)-1H-benzoimidazole

HRID 2202470Notes

Reaction equation

HRID 2202470 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)[C:6]=2[CH:20]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:32](B(O)O)=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[C:32]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[CH:8][N:7]([C:10]5[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=5)[C:6]=4[CH:20]=3)=[CH:31][CH:30]=[N:29]2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 900951701-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid2×HCID 900952186-bromo-1-(4-trifluoromethyl-phenyl)-1H-benzo[d]imidazole2×

Product 1

HCID 736736736-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-(4-trifluoromethyl-phenyl)-1H-benzoimidazole

Procedure

The title compound, light brown solid (67 mg, 54%), MS (ISP) m/z=423.3 [(M+H)+], mp 204° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(4-trifluoromethyl-phenyl)-1H-benzo[d]imidazole (intermediate I) (100 mg, 293 μmol) and 1-(4-fluoro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate A) (72.5 mg, 352 μmol).

Sources & evidence

ORD record
ord-50ddf159acd74ff7b14c10142128aee2
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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