Phenylacetonitrile → 3-Phenyl-5-(2-phenyl-2H-pyrazol-3-yl)-benzo[c]isoxazole

HRID 59850Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=O.[C:21]1([CH2:27]C#N)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:21]1([C:27]2[O:3][N:1]=[C:4]3[CH:9]=[CH:8][C:7]([C:10]4[N:14]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[N:13]=[CH:12][CH:11]=4)=[CH:6][C:5]=23)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Reactant 2

HCID 8794Phenylacetonitrile

HCID 132872195-(4-Nitrophenyl)-1-phenyl-1H-pyrazole2×

Product 1

HCID 730509603-Phenyl-5-(2-phenyl-2H-pyrazol-3-yl)-benzo[c]isoxazole

Procedure

The title compound, light grey solid (37 mg, 29%), MS (ISP) m/z=338.3 [(M+H)+], mp 163° C., was prepared in accordance with the general method of example 1 from 5-(4-nitro-phenyl)-1-phenyl-1H-pyrazole (intermediate A) (100 mg, 353 μmol) and commercially available 2-phenyl-acetonitrile.

Sources & evidence

ORD record: ord-6205c395f8cb41608996a9d2a6bc054c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440962B2

Reaction notes

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