反応式
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[Li+].CC([N-]C(C)C)C.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[Cl:21].C1([CH:25]=[N:26][S:27]([CH3:30])(=[O:29])=[O:28])CC1.CI>C1COCC1.O>[Br:14][C:15]1[C:20]([Cl:21])=[C:19]([CH:2]([CH:3]2[CH2:5][CH2:4]2)[N:26]([CH3:25])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:18]=[N:17][CH:16]=1参加物
反応条件
- 温度
- -78 °C
実験手順
To a solution of DIPA (1.71 mL, 12 mmol) in THF (50 mL) at −78° C. was added 1.6M BuLi (7.5 mL, 12.0 mmol) and the mixture was stirred at −78° C. for 2 h. The LDA solution was cannulated into a solution of 3-bromo-4-chloropyridine (2.117 g, 11 mmol) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of N-(cyclopropylmethylene)methanesulfonamide (10 mmol, crude mixture) in THF (50 mL) was added and the mixture was stirred at −78° C. for 1 h. A solution of MeI (0.625 mL, 10 mmol) in THF (10 mL) was added, and the mixture was warmed to room temperature and stirred overnight. Water (0.5 mL) was added and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a 0-50% EtOAc-heptane gradient to give N-((5-bromo-4-chloropyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide. MS (ESI): m/z 353.0, 355.0 (M+H)+.
後処理
- stirringthe mixture was stirred at −78° C. for 1 h
- stirringthe mixture was stirred at −78° C. for 1 h
- temperaturethe mixture was warmed to room temperature
- stirringstirred overnight
- concentrationthe mixture was concentrated in vacuo
- customThe residue was purified by silica gel chromatography
- washeluting with a 0-50% EtOAc-heptane gradient
出典と根拠
- ORDレコード
- ord-4d2480c9553a40798ecae9f1c0e51ad7
- 出典データセット
- uspto-grants-2013_02
- 特許番号
- US08383827B2
関連ノート
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