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

HRID 59820Notes

Reaction equation

HRID 59820 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=[O:20])=[CH:15][CH:14]=2)=[CH:11][CH:10]=[N:9]1.[F:22][C:23]([F:34])([F:33])[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]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]3=[N:19][O:20][C:30]([C:27]4[CH:26]=[CH:25][C:24]([C:23]([F:22])([F:33])[F:34])=[CH:29][CH:28]=4)=[C:15]3[CH:14]=2)=[CH:11][CH:10]=[N:9]1

Participants

3

Reactant 2

HCID 753594-(Trifluoromethyl)phenylacetonitrileHCID 900327651-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730528465-[2-(2-Fluoro-phenyl)-2H-pyrazol-3-yl]-3-(4-trifluoromethyl-phenyl)-benzo[c]isoxazole

Procedure

The title compound, light brown solid (88 mg, 59%), MS (ISP) m/z=424.2 [(M+H)+], mp 156° C., was prepared in accordance with the general method of example 1 from 1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate B) (100 mg, 353 μmol) and commercially available 2-(4-trifluoromethyl-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-4daccd8a564b4ba6ab7529050e8e9d0d
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

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