4-(6-Bromoimidazo[1,2-a]pyridin-3-yl)benzonitrile → 4-{6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-imidazo [1,2-a]pyridin-3-yl}-benzonitrile

HRID 629287Notes

Reaction equation

HRID 629287 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[CH:7]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]5[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=5)=[CH:9][N:10]=4)[CH:7]=3)=[CH:29][CH:28]=[N:27]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 898271504-(6-Bromoimidazo[1,2-a]pyridin-3-yl)benzonitrile2×HCID 901893681-(4-fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 760724594-{6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-imidazo [1,2-a]pyridin-3-yl}-benzonitrile

Procedure

The title compound, white solid (88 mg, 69%), MS (ISP) m/z=380.5 [(M+H)+], mp 215° C., was prepared in accordance with the general method of example 1 from 4-(6-bromo-imidazo[1,2-a]pyridin-3-yl)-benzonitrile (intermediate N) (0.1 g, 0.335 mmol) and 1-(4-fluoro-phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate A) (0.13 mg, 0.44 mmol).

Sources & evidence

ORD record
ord-f38a070d2a76408eadf8f59e6cf62891
Source dataset
uspto-grants-2016_04
Patent number
US09315502B2

Reaction notes

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