반응식
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.N1C=CC=CC=1.C(N(CC)CC)C.[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][NH:28][C:29]=1[C:30]([F:33])([F:32])[F:31])=[O:24])[CH3:21]>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:20]([O:22][C:23]([C:25]1[C:29]([C:30]([F:32])([F:33])[F:31])=[N:28][N:27]([CH:1]2[CH2:3][CH2:2]2)[CH:26]=1)=[O:24])[CH3:21]참가 물질
반응 조건
- 온도
- 60 °C
실험 절차
Cyclopropyl boronic acid (11 g, 127 mmol), Copper acetate (17.4 g, 95.7 mmol), Pyridine (17.7 g, 223 mmol) and triethylamine (22.4 mL, 160 mmol) were added successively to a solution of 5-Trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (Preparation 143, 6.63 g, 31.9 mmol) in THF (70 mL) and the resulting mixture was allowed to stir at 60° C. for 36 hours. The reaction mixture was filtered over a celite bed and filtrate was concentrated in vacuo and diluted with EtOAc (200 mL). The organic layer was washed with 1N HCl (1×25 mL), brine (1×25 mL) and dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (Hexane:EtOAc 85:15) to afford the title compound as brown solid in 29% yield, 2.3 g.
후처리
- filtrationThe reaction mixture was filtered over a celite bed and filtrate
- concentrationwas concentrated in vacuo
- additiondiluted with EtOAc (200 mL)
- washThe organic layer was washed with 1N HCl (1×25 mL), brine (1×25 mL)
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customThe crude material was purified by column chromatography on silica gel (Hexane:EtOAc 85:15)
출처 및 근거
- ORD 기록
- ord-69ea88621ecb4df4baede86370c9f0af
- 출처 데이터셋
- uspto-grants-2014_09
- 특허 번호
- US08846698B2
연결된 노트
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