反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(C(C)C)C(C)C.[C:22](Br)([CH3:25])([CH3:24])[CH3:23]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].C1(C)C=CC=CC=1.[O-]S(C(F)(F)F)(=O)=O.[Zn+2].[O-]S(C(F)(F)F)(=O)=O>[C:22]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)([CH3:25])([CH3:24])[CH3:23]参加物
7
反応条件
- 温度
- 120 °C
実験手順
To a mixture of 6-nitroindole (1 g, 6.2 mmol), zinc triflate (2.06 g, 5.7 mmol) and TBAI (1.7 g, 5.16 mmol) in anhydrous toluene (11 mL) was added DIEA (1.47 g, 11.4 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 10 min at 120° C., followed by addition of t-butyl bromide (0.707 g, 5.16 mmol). The resulting mixture was stirred for 45 min at 120° C. The solid was filtered off and the filtrate was concentrated to dryness and purified by column chromatography on silica gel (Pet.Ether./EtOAc 20:1) to give 3-tert-butyl-6-nitro-1H-indole as a yellow solid (0.25 g, 19%). 1H NMR (CDCl3) δ 8.32 (d, J=2.1 Hz, 1H), 8.00 (dd, J=2.1, 14.4 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.25 (s, 1H), 1.46 (s, 9H).
後処理
- stirringThe resulting mixture was stirred for 45 min at 120° C
- filtrationThe solid was filtered off
- concentrationthe filtrate was concentrated to dryness
- custompurified by column chromatography on silica gel (Pet.Ether./EtOAc 20:1)
出典と根拠
- ORDレコード
- ord-f2ad71930ecb4773ba351e9d93c9dc4e
- 出典データセット
- uspto-grants-2014_09
- 特許番号
- US08829204B2
関連ノート
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