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

HRID 59825

Reaction equation

HRID 59825 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=[O:20])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]C#N)=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:20][N:19]=[C:16]3[CH:17]=[CH:18][C:13]([C:12]4[N:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=5)[N:9]=[CH:10][CH:11]=4)=[CH:14][C:15]=23)=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 68016Benzeneacetonitrile, 4-fluoro-HCID 900335601-(3-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730528503-(4-Fluoro-phenyl)-5-[2-(3-fluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

Procedure

The title compound, light grey solid (74 mg, 56%), MS (ISP) m/z=374.1 [(M+H)+], mp 175° C., was prepared in accordance with the general method of example 1 from 1-(3-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate D) (100 mg, 353 μmol) and commercially available 2-(4-fluoro-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-50f4e03be1fd47fea3f8855c699d71d5
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Linked notes

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