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

HRID 59836Notes

Reaction equation

HRID 59836 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=[O:21])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]C#N)=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:21][N:20]=[C:17]3[CH:18]=[CH:19][C:14]([C:13]4[N:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[N:10]=[CH:11][CH:12]=4)=[CH:15][C:16]=23)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 68016Benzeneacetonitrile, 4-fluoro-HCID 900327501-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730531503-(4-Fluoro-phenyl)-5-[2-(4-methoxy-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

Procedure

The title compound, light green solid (51 mg, 39%), MS (ISP) m/z=386.2 [(M+H)+], mp 179° C., was prepared in accordance with the general method of example 1 from 1-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate G) (100 mg, 353 μmol) and commercially available 2-(4-fluoro-phenyl)-acetonitrile.

Sources & evidence

ORD record
ord-6819518e924147a884fd567ffba2a050
Source dataset
uspto-grants-2016_09
Patent number
US09440962B2

Reaction notes

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