反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]#[N:25])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.O.[N:27]([Na])=[N+:28]=[N-:29]>CS(C)=O.Br[Zn]Br>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24]4[N:27]=[N:28][NH:29][N:25]=4)[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1参加物
6
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 125 °C
実験手順
To a solution of (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile (100 mg, 0.30 mmol) in DMSO (10 mL) was added dibromozinc (33.8 mg, 0.15 mmol), water (10 mL), azidosodium (48.8 mg, 0.75 mmol) and water (5 mL). The resulting solution was stirred for 1 days at 125° C. and then quenched by the addition of water (100 mL), extracted with dichloromethane (3×30 mL). The organic layers were combined and dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2% dichloromethane in methanol) to afford (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)-6-(2H-tetrazol-5-yl)quinoxaline as a yellow solid (70.9 mg, 63%).
後処理
- customquenched by the addition of water (100 mL)
- extractionextracted with dichloromethane (3×30 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto give a residue, which
- customwas purified via silica gel column chromatography (2% dichloromethane in methanol)
出典と根拠
- ORDレコード
- ord-c9bee96bffa14a1fb7fe9c4edfb7a55f
- 出典データセット
- uspto-grants-2014_12
- 特許番号
- US08916561B2
関連ノート
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