4-Chlorobenzyl cyanide → 3-(4-Chloro-phenyl)-5-[2-(2,4-difluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

HRID 59848Notes

Reaction equation

HRID 59848 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=[O:21])=[CH:16][CH:15]=2)=[CH:12][CH:11]=[N:10]1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]C#N)=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:21][N:20]=[C:17]3[CH:18]=[CH:19][C:14]([C:13]4[N:9]([C:3]5[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=5[F:1])[N:10]=[CH:11][CH:12]=4)=[CH:15][C:16]=23)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 2415824-Chlorobenzyl cyanideHCID 900332241-(2,4-difluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730509573-(4-Chloro-phenyl)-5-[2-(2,4-difluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

Procedure

The title compound, light green solid (71 mg, 53%), MS (ISP) m/z=408.2 [(M+H)+], mp 155° C., was prepared in accordance with the general method of example 1 from 1-(2,4-difluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate I) (100 mg, 353 μmol) and commercially available 2-(4-chloro-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-8d9a194436624660acf87da5e8475e37
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

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