1-(3-Fluoro-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione → 5-(3-Fluoro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 2054229Notes

Reaction equation

HRID 2054229 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12](=O)[CH2:13][C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[NH2:21][C:22]1[C:26]([C:27]#[N:28])=[CH:25][NH:24][N:23]=1>>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[N:23]3[N:24]=[CH:25][C:26]([C:27]#[N:28])=[C:22]3[N:21]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]

Participants

3

Reactant 2

HCID 865986571-(3-Fluoro-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dioneHCID 178510443HCID 178510443, compound

Product 1

HCID 865986565-(3-Fluoro-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 37.1%

Procedure

Reaction of 1-(3-fluoro-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (302 mg, 1.0 mmol), prepared from commercially available 3-fluoro-4-trifluoromethyl-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 an off-white solid (139 mg, 37%). MS (ISP) 375.0 [(M+H)+]; mp 184° C.

Sources & evidence

ORD record
ord-4cbddc69ef8d4ed99f1d2c549841853b
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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