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

HRID 629291Notes

Reaction equation

HRID 629291 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]([F:17])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:26]2[N:30]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=3)[N:29]=[CH:28][CH:27]=2)O1>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[N:6]3[CH:7]=[C:2]([C:26]4[N:30]([C:31]5[CH:32]=[CH:33][C:34]([C:37]([F:38])([F:39])[F:40])=[CH:35][CH:36]=5)[N:29]=[CH:28][CH:27]=4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 901891376-Bromo-3-(4-fluorophenyl)-imidazo[1,2-a]pyridine2×HCID 901894005-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole2×

Product 1

HCID 760724283-(4-Fluoro-phenyl)-6-[2-(4-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-imidazo[1,2-a]pyridine

Procedure

The title compound, white solid (37 mg, 26%), MS (ISP) m/z=423.6 [(M+H)+], mp 147° C., was prepared in accordance with the general method of example 1 from 6-bromo-3-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine (intermediate E) (0.1 mg, 0.34 mmol) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(4-trifluoromethyl-phenyl)-1H-pyrazole (intermediate P) (0.15 g, 0.45 mmol).

Sources & evidence

ORD record
ord-ef71e8ca11da464abaa125ad78642649
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

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