4-(Trifluoromethyl)phenylacetonitrile → 5-[2-(2,4-Difluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-trifluoromethyl-phenyl)-benzo[c]isoxazole

HRID 59847Notes

Reaction equation

HRID 59847 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.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31]C#N)=[CH:27][CH:26]=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:21][C:31]([C:28]4[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:34])[F:35])=[CH:30][CH:29]=4)=[C:16]3[CH:15]=2)=[CH:12][CH:11]=[N:10]1

Participants

3

Reactant 2

HCID 753594-(Trifluoromethyl)phenylacetonitrileHCID 900332241-(2,4-difluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730509565-[2-(2,4-Difluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-trifluoromethyl-phenyl)-benzo[c]isoxazole

Procedure

The title compound, light yellow solid (18 mg, 12%), MS (ISP) m/z=442.2 [(M+H)+], mp 159° 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-trifluoromethyl-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-f115a77c93cf4e03a89447568917deaa
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

Loading…