Dimethylformamide → 6-chloro-5-fluoro-1H-indole-3-carbaldehyde
反応式
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][C:8]=1[F:16].CN(C)[CH:19]=[O:20]>>[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([CH:19]=[O:20])=[CH:12][NH:13]2)=[CH:9][C:8]=1[F:16]参加物
反応条件
- 温度
- 35 °C
実験手順
POCl3 (2.43 mL, 26.53 mmol) was added dropwise to N,N-dimethylformamide (15.0 mL) at −20° C. and stirred below −5° C. for one hour. A solution of 6-chloro-5-fluoroindole (3.0 g, 17.69 mmol) in dimethylformamide (5.0 mL) was added dropwise to the above reaction mixture at −20° C. The salt-ice bath was removed and the reaction mixture was warmed to 35° C., After one hour, the reaction was poured onto ice and basified by solid sodium bicarbonate and extracted with ethyl acetate. The combined organic layer was washed with water and then concentrated to give 6-chloro-5-fluoro-1H-indole-3-carbaldehyde (3.4 g, 97%) as a light brown solid. 1H NMR (500 MHz, CDCl3): δ 10.02 (s, 1 H), 8.10 (d, 1H, J=9.5 Hz), 7.87 (s, 1 H), 7.49 (d, 1H, J=5.5 Hz).
後処理
- customThe salt-ice bath was removed
- additionthe reaction was poured onto ice
- extractionextracted with ethyl acetate
- washThe combined organic layer was washed with water
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-8389b12003694299beff62bd387146b2
- 出典データセット
- uspto-grants-2011_11
- 特許番号
- US08053442B2
反応ノート
読み込み中…