4,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dione → 5-(4-Fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2108396Notes

Reaction equation

HRID 2108396 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[NH2:17][C:18]1[C:22]([C:23]#[N:24])=[CH:21][NH:20][N:19]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:19]3[N:20]=[CH:21][C:22]([C:23]#[N:24])=[C:18]3[N:17]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27714764,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dioneHCID 178510443HCID 178510443, compound

Product 1

HCID 47663045-(4-Fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 39%

Procedure

Reaction of 1-(4-fluoro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (234 mg, 1.0 mmol), prepared from commercially available 4-fluoro-acetophenone according to general procedure A, and 3-amino-4-cyano-pyrazole (108 mg, 1.0 mmol) according to general procedure B yielded the title compound as a yellow solid (118 mg, 39%). MS (ISP) 306.9 [(M+H)+]; mp 198° C.

Sources & evidence

ORD record
ord-247e1ebe13e3447d8bd0bb46c6a8788a
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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