反応式
[CH3:1][S:2]([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])O.[Na+].[N:30]#[C:31]Br>ClCCl.O>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:31]#[N:30])[CH2:19][CH2:18]3)=[CH:13][N:12]=2)=[CH:23][CH:24]=1)(=[O:3])=[O:4]参加物
反応条件
- 温度
- 0 °C
実験手順
To a solution of 4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidine (124 mg, 0.358 mmol) in dichloromethane (1 mL) was added a solution of sodium hydrogen carbonate (60 mg, 0.716 mmol) in water (0.5 mL). The mixture was cooled in an ice bath followed by the addition of a solution of cyanogen bromide (45 mg, 0.430 mmol) in dichloromethane (1 mL). The mixture was stirred at 0° C. for 30 minutes and then stirred at room temperature for an additional 1 hour. The mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (114 mg, yield 86%).
後処理
- temperatureThe mixture was cooled in an ice bath
- stirringstirred at room temperature for an additional 1 hour
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate)
出典と根拠
- ORDレコード
- ord-cf10702caf9c415fbe8aacbc35050d46
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08536176B2
関連ノート
読み込み中…