Water → 5-bromo-6-chloro-1H-indole-3-carbaldehyde

HRID 1054560노트

반응식

HRID 1054560 반응식
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[NH:12][CH:11]=[CH:10]2.[OH-].[Na+].O.CN([CH:23]=[O:24])C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Cl:16])[NH:12][CH:11]=[C:10]2[CH:23]=[O:24]

참가 물질

6

반응물 5

HCID 962WaterHCID 6228Dimethylformamide2회HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 144196195-Bromo-6-chloro-1H-indole

생성물 1

HCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehyde수율 90%

실험 절차

A round-bottom flask was charged with DMF (54 mL). Phosphorus oxychloride (6.21 mL, 66.8 mmol) was added dropwise over 5 minutes, and the reaction mixture was stirred at room temperature for an additional 5 minutes. A solution of 5-bromo-6-chloro-1H-indole (7700 mg, 33.41 mmol) in DMF (7 mL) was added dropwise to the reaction mixture, which caused a precipitate to form. The reaction mixture was then heated to 95° C. for 25 minutes. The reaction mixture was treated with 1 N aqueous sodium hydroxide (170 mL) and water (170 mL). The reaction mixture was stirred at 95° C. for 11 minutes. The reaction mixture was cooled to 0° C., and the solids were collected by filtration. The solids were washed with water (50 mL) and diethyl ether (50 mL) and dried in vacuo for 16 hours at 65° C. to afford the title compound (7.77 g, 90%) as a tan solid. MS (AP+) 257.9 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 9.93 (s, 1H), 8.40 (s, 1H), 8.38 (s, 1H), 7.80 (s, 1H).

후처리

  1. customto form
  2. temperatureThe reaction mixture was then heated to 95° C. for 25 minutes
  3. stirringThe reaction mixture was stirred at 95° C. for 11 minutes
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. filtrationthe solids were collected by filtration
  6. washThe solids were washed with water (50 mL) and diethyl ether (50 mL)
  7. customdried in vacuo for 16 hours at 65° C.

출처 및 근거

ORD 기록
ord-cd9104f313074c1ca5483818012a7674
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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