Benzeneacetonitrile, 4-fluoro- → 5-[2-(2,4-Difluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-fluoro-phenyl)-benzo[c]isoxazole

HRID 59844Notes

Reaction equation

HRID 59844 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-:22])=O)=[CH:16][CH:15]=2)=[CH:12][CH:11]=[N:10]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]C#N)=[CH:26][CH:25]=1>>[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]3=[N:20][O:22][C:30]([C:27]4[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=4)=[C:16]3[CH:15]=2)=[CH:12][CH:11]=[N:10]1

Participants

3

Reactant 2

HCID 68016Benzeneacetonitrile, 4-fluoro-HCID 900332241-(2,4-difluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730532955-[2-(2,4-Difluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-fluoro-phenyl)-benzo[c]isoxazole

Procedure

The title compound, light grey solid (22 mg, 17%), MS (ISP) m/z=392.2 [(M+H)+], mp 149° 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-fluoro-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-3427a8f1543647a382dd529af7ab6165
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

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