1-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol → 1-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-one

HRID 1506230노트

반응식

HRID 1506230 반응식
[Cl:1][C:2]1[C:7]([CH:8]([OH:11])[CH2:9][CH3:10])=[CH:6][N:5]=[C:4]2[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:3]=12>COCCOC.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][N:5]=[C:4]2[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:14][C:3]=12

참가 물질

4

반응물 1

HCID 712584341-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol

생성물 1

HCID 712584601-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-one수율 53%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

1-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol (75.6 mg, 0.222 mmol) in 1,2-dimethoxyethane (5 mL) was vigorously stirred with manganese dioxide (450 mg, 5.17 mmol) at 60° C. for 3 hours and then at 80° C. for 3 hours. The reaction mixture was filtered, the solid was washed with chloroform, and the filtrate and the washings were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1 (v/v)) to give the title compound as a colorless oil (39.9 mg, yield 53%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with chloroform
  3. concentrationthe filtrate and the washings were concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1 (v/v))

출처 및 근거

ORD 기록
ord-4eb4bfde65924d56b57f1d976194f556
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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