Dimethylformamide → 6-chloro-5-fluoro-1H-indole-3-carbaldehyde

HRID 555336노트

반응식

HRID 555336 반응식
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]

참가 물질

4

반응물 3

HCID 6228Dimethylformamide2회HCID 24813Phosphorus oxychlorideHCID 27736486-Chloro-5-fluoro-1H-indole

생성물 1

HCID 210715286-chloro-5-fluoro-1H-indole-3-carbaldehyde수율 97%

반응 조건

온도
35 °C

실험 절차

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).

후처리

  1. customThe salt-ice bath was removed
  2. additionthe reaction was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with water
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8389b12003694299beff62bd387146b2
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053442B2

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