1-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione → 3-Bromo-5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

HRID 558548Notes

Reaction equation

HRID 558548 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:14](=O)[CH2:15][C:16](=O)[C:17]([F:20])([F:19])[F:18])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH3:2].[NH2:23][C:24]1[C:28]([Br:29])=[CH:27][NH:26][N:25]=1>>[Br:29][C:28]1[CH:27]=[N:26][N:25]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([C:6]3[CH:7]=[CH:8][C:9]([C:10]([F:13])([F:12])[F:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)=[N:23][C:24]=12

Participants

3

Reactant 2

HCID 865986761-(3-Ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dioneHCID 178509245HCID 178509245, compound

Product 1

HCID 866079943-Bromo-5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 92.8%

Procedure

Prepared from 1-(3-ethoxy-4-trifluoromethyl-phenyl)-4,4,4-trifluoro-butane-1,3-dione (example C.3 step 1) (8.00 g, 24 mmol) and commercially available 3-amino-4-bromopyrazole (4.03 g, 24 mmol) as described in example C.1 step 2a to give the 3-bromo-5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (10.12 g, 91%) as a yellow solid. MS (ISP) 454.0 [(M+H)+] and 456.0 [(M+2+H)+].

Sources & evidence

ORD record
ord-011d577d5daf4897accd81428a2e5d1c
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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