1-(3-Fluoro-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione → 5-(3-Fluoro-4-trifluoromethyl-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2054263Notes

Reaction equation

HRID 2054263 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]2[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=2)=[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]4[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([CH3:34])[CH:28]=4)=[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 178422939HCID 178422939, compound

Product 1

HCID 112824395-(3-Fluoro-4-trifluoromethyl-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 20.2%

Procedure

Reaction of 1-(3-fluoro-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (151 mg, 0.5 mmol), prepared from commercially available 3-fluoro-4-trifluoromethyl-acetophenone according to general procedure A, and 3-amino-4-(2,6-dimethyl-4-pyridinyl)-pyrazole [prepared from 4-cyanomethyl-2,6-dimethyl-pyridine, CAS No. 130138-46-4, see part synthesis of amino-pyrazole derivatives] (94 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (46 mg, 20%). MS (ISP) 455.0 [(M+H)+]; mp 245° C.

Sources & evidence

ORD record
ord-e8b980a0f4d6457ea81e62b09d3f6df6
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

Loading…