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[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Cl[C:16]1[N:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:17]=1[C:18]#[N:19]>C1COCC1>[C:18]([C:17]1[C:16]([CH:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:23][CH:22]=[C:21]([C:24]([F:27])([F:25])[F:26])[CH:20]=1)#[N:19]참가 물질
실험 절차
To a suspension of sodium hydride (0.752 g, 29.8 mmol) in THF (18 mL) under nitrogen was added dropwise a solution of tert-butyl methyl malonate (3.18 mL, 17.9 mmol) in dry THF (15 mL) via syringe during a period of 15 min. The reaction mixture was stirred for 30 min before a solution of 2-chloro-5-(trifluoromethyl)nicotinonitrile (4.0 g, 14.5 mmol) in THF (30 mL) was added slowly. After being stirred at room temperature overnight, the reaction mixture was quenched with aqueous NH4Cl. THF was removed in vacuo and the aqueous solution was extracted with EtOAc three times. The combined organic layers were dried over MgSO4, filtered, and evaporated in vacuo. The crude brown product (7.1 g) was purified by flash chromatography (10:90 EtOAc/hexanes) to afford 4.20 g (84%) of desired product as a yellow oil. LC-MS calculated for C15H15F3N2O4: (M+H)+345; found 245.0 (M−CO2tBu+H+1)+.
후처리
- additionwas added slowly
- customthe reaction mixture was quenched with aqueous NH4Cl
- customTHF was removed in vacuo
- extractionthe aqueous solution was extracted with EtOAc three times
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- customevaporated in vacuo
- customThe crude brown product (7.1 g) was purified by flash chromatography (10:90 EtOAc/hexanes)
출처 및 근거
- ORD 기록
- ord-7a7a78feaa6b44d6bc3fb66f3fac6f9a
- 출처 데이터셋
- uspto-grants-2007_12
- 특허 번호
- US07307086B2
연결된 노트
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