反応式
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.N1C=CC=CC=1.C(N(CC)CC)C.[F:20][C:21]([F:33])([F:32])[C:22]1[NH:26][N:25]=[CH:24][C:23]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:30]([O:29][C:27]([C:23]1[C:22]([C:21]([F:20])([F:32])[F:33])=[N:26][N:25]([CH:1]2[CH2:3][CH2:2]2)[CH:24]=1)=[O:28])[CH3:31]参加物
反応条件
- 温度
- 60 °C
実験手順
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 ethyl 5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (Preparation 100, 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 silica gel column chromatography eluting with Hexane:EtOAc 85:15 to afford the title compound as brown solid (29%, 2.3 g).
後処理
- 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 silica gel column chromatography
- washeluting with Hexane:EtOAc 85:15
出典と根拠
- ORDレコード
- ord-df9f425fe476459bb01e612ffc5742ed
- 出典データセット
- uspto-grants-2015_10
- 特許番号
- US09163021B2
関連ノート
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