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

HRID 2054218Notes

Reaction equation

HRID 2054218 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:7][CH:8]=1.[NH2:20][C:21]1[C:25]([C:26]#[N:27])=[CH:24][NH:23][N:22]=1>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:22]3[N:23]=[CH:24][C:25]([C:26]#[N:27])=[C:21]3[N:20]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 162279574,4,4-Trifluoro-1-[3-(trifluoromethyl)phenyl]butane-1,3-dioneHCID 178510443HCID 178510443, compound

Product 1

HCID 865986545-(3-Trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 42.4%

Procedure

Reaction of 1-(3-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (284 mg, 1.0 mmol), prepared from commercially available 3-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 a white solid (151 mg, 42%). MS (ISP) 357.0 [(M+H)+]; mp 192° C.

Sources & evidence

ORD record
ord-69be2f042a514a7a955820701e2966f9
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

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