1-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dione → 5-(4-Chloro-phenyl)-3-(2-methyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 2108442Notes

Reaction equation

HRID 2108442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[NH2:17][C:18]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=2)=[CH:21][NH:20][N:19]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:19]3[N:20]=[CH:21][C:22]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=4)=[C:18]3[N:17]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27738321-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 178422940HCID 178422940, compound

Product 1

HCID 114860555-(4-Chloro-phenyl)-3-(2-methyl-pyridin-4-yl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 43.2%

Procedure

Reaction of 1-(4-chloro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (125 mg, 0.5 mmol), prepared from commercially available 4-chloro-acetophenone according to general procedure A, and 3-amino-4-(2-methyl-4-pyridinyl)-pyrazole [see part synthesis of amino-pyrazole derivatives] (87 mg, 0.5 mmol) according to general procedure B yielded the title compound as a yellow solid (84 mg, 43%). MS (ISP) 389.1 [(M+H)+]; mp 220° C.

Sources & evidence

ORD record
ord-f75ed89131084f95889ef4d0acb85ce8
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

Loading…