1-(3-Chloro-4-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione → 5-(3-Chloro-4-fluoro-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2054259Notes

Reaction equation

HRID 2054259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:18][C:19]1[C:23]([C:24]2[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[CH:25]=2)=[CH:22][NH:21][N:20]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:12]([F:15])([F:14])[F:13])[N:20]3[N:21]=[CH:22][C:23]([C:24]4[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([CH3:31])[CH:25]=4)=[C:19]3[N:18]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 129216971-(3-Chloro-4-fluorophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 178422939HCID 178422939, compound

Product 1

HCID 114529115-(3-Chloro-4-fluoro-phenyl)-3-(2,6-dimethyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 46.1%

Procedure

Reaction of 1-(3-chloro-4-fluoro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (134 mg, 0.5 mmol), prepared from commercially available 3-chloro-4-fluoro-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 (97 mg, 46%). MS (ISP) 421.1 [(M+H)+]; mp 271° C.

Sources & evidence

ORD record
ord-4e4574f0410044e9a556e3ed8aeca3c3
Source dataset
uspto-grants-2008_02
Patent number
US07329662B2

Reaction notes

Loading…