4,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione → 3-Bromo-7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 268984Notes

Reaction equation

HRID 268984 reaction equation
[F:1][CH:2]([F:18])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[NH2:19][C:20]1[C:24]([Br:25])=[CH:23][NH:22][N:21]=1>>[Br:25][C:24]1[CH:23]=[N:22][N:21]2[C:3]([CH:2]([F:18])[F:1])=[CH:4][C:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=3)=[N:19][C:20]=12

Participants

3

Reactant 2

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dioneHCID 178509245HCID 178509245, compound

Product 1

HCID 866079933-Bromo-7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidineYield 92.9%

Procedure

Prepared from 4,4-difluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (example C.2 step 1) (21.40 g, 80 mmol) and commercially available 3-amino-4-bromopyrazole (13.29 g, 80 mmol) as described in example C.1, step 2a to give 3-bromo-7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (29.14 g, 92%) as a yellow solid. MS (ISP) 392.0 [(M+H)+], 394.0 [(M+2+H)+].

Sources & evidence

ORD record
ord-39087b2005ae426383977ab7c5f6b7af
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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