反応式
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[CH3:31][S:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:37]([C:36]2[CH:39]=[CH:40][C:33]([S:32][CH3:31])=[CH:34][CH:35]=2)[OH:38])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
To a solution of 1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridine (3 g, 10.87 mmol) in dry tetrahydrofuran (40 mL) at −78° C. was added a solution of n-butyllithium in n-hexane (2.5 M, 6.8 mL 17 mmol). The mixture was stirred at −78° C. for 35 min and then treated with 4-methylsulfanyl-benzaldehyde (2.8 mL, 21.0 mmol) dropwise. The resulting mixture was stirred at −78° C. for 1 h and quenched with brine. The mixture was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes) afforded (1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanol as a white solid (2.1 g, 45.2%): LC/MS m/e calcd for C21H17FN2O3S2 [M+H]+ 429.51, observed 428.7.
後処理
- stirringThe resulting mixture was stirred at −78° C. for 1 h
- customquenched with brine
- extractionThe mixture was extracted with ethyl acetate (2×200 mL)
- washwashed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 20% ethyl acetate/hexanes)
出典と根拠
- ORDレコード
- ord-d1b73b84a50d46dbad4e8656e3582e52
- 出典データセット
- uspto-grants-2012_07
- 特許番号
- US08222416B2
関連ノート
読み込み中…