Dimethylformamide → 7-bromo-5-(trifluoromethyl)-1H-indole-3-carbaldehyde
反応式
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2.CN([CH:23]=[O:24])C>>[Br:6][C:7]1[CH:8]=[C:9]([C:16]([F:19])([F:17])[F:18])[CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH:23]=[O:24]参加物
反応条件
- 温度
- 0 °C
実験手順
Phosphorus oxychloride (1.029 ml, 11.04 mmol) was added dropwise to DMF (8 ml) at 0° C. The mixture was stirred 30 min at 0° C. and 7-bromo-5-(trifluoromethyl)-1H-indole (2.65 g, 10.04 mmol) in DMF (2 mL) was added dropwise. The cooling bath was removed and the reaction was stirred at ambient temperature for 3 hours. The reaction was quenched with ice (5 g) and aqueous sodium hydroxide (1N, 20 mL). The reaction was extracted with ethyl acetate (2×30 mL) and the organic phase was dried with MgSO4 and evaporated. The residue was purified by chromatography on SiO2 with a 5%-60% gradient of ethyl acetate/hexanes. The product 7-bromo-5-(trifluoromethyl)-1H-indole-3-carbaldehyde (2.17 g, 7.43 mmol, 74.0% yield) was obtained as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 10.09 (s, 1H), 9.06 (s, 1H), 8.59 (s, 1H), 8.00 (d, J=3.2 Hz, 1H), 7.72 (d, J=3.0 Hz, 1H). LC/MS (HPLC method 4): tR=3.29 min, 292.06(MH)+.
後処理
- customThe cooling bath was removed
- stirringthe reaction was stirred at ambient temperature for 3 hours
- customThe reaction was quenched with ice (5 g) and aqueous sodium hydroxide (1N, 20 mL)
- extractionThe reaction was extracted with ethyl acetate (2×30 mL)
- dry with materialthe organic phase was dried with MgSO4
- customevaporated
- customThe residue was purified by chromatography on SiO2 with a 5%-60% gradient of ethyl acetate/hexanes
出典と根拠
- ORDレコード
- ord-453c2eb8b682466db06ce1afdcb09050
- 出典データセット
- uspto-grants-2011_09
- 特許番号
- US08026257B2
反応ノート
読み込み中…