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

HRID 59823Notes

Reaction equation

HRID 59823 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-:21])=O)=[CH:15][CH:14]=2)=[CH:11][CH:10]=[N:9]1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]C#N)=[CH:25][CH:24]=1>>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:21][N:19]=[C:16]3[CH:15]=[CH:14][C:13]([C:12]4[N:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])[N:9]=[CH:10][CH:11]=4)=[CH:18][C:17]=23)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 27914Benzeneacetonitrile, 4-bromo-HCID 900327651-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730528483-(4-Bromo-phenyl)-5-[2-(2-fluoro-phenyl)-2H-pyrazol-3-yl]benzo[c]isoxazole

Procedure

The title compound, light yellow solid (108 mg, 71%), MS (ISP) m/z=434.2 [(M+H)+], mp 202° 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-bromo-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-5a4c4081712a4f74bdcac9f27f2b5dfd
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

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