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

HRID 629274Notes

Reaction equation

HRID 629274 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.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=[N:26]2)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[C:29]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]5[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=5)=[CH:9][N:10]=4)[CH:7]=3)=[CH:28][CH:27]=[N:26]2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 901891376-Bromo-3-(4-fluorophenyl)-imidazo[1,2-a]pyridine2×HCID 901893311-(4-chlorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 760725236-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-3-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine

Procedure

The title compound, white solid (27 mg, 20%), MS (ISP) m/z=389.4 [(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 1-(4-chloro-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (intermediate B) (0.13 g, 0.41 mmol).

Sources & evidence

ORD record
ord-6664a62faa604e04ad06d458495dfe6c
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

Loading…