1-(4-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 629286Notes

Reaction equation

HRID 629286 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:32](B3OC(C)(C)C(C)(C)O3)=[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:6]([C:8]([C:11]5[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=5)=[CH:9][N:10]=4)[CH:7]=3)=[CH:31][CH:30]=[N:29]2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 901893681-(4-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 901898656-Bromo-3-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine2×

Product 1

HCID 760724906-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

Procedure

The title compound, off-white solid (87 mg, 70%), MS (ISP) m/z=423.5 [(M+H)+], mp 172° C., was prepared in accordance with the general method of example 1 from 6-bromo-3-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine (intermediate M) (0.1 g, 0.29 mmol) and 1-(4-fluoro-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate A) (0.11 mg, 0.38 mmol).

Sources & evidence

ORD record
ord-0fec449f20ba459a995154421d8e7257
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

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