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

HRID 1506229노트

반응식

HRID 1506229 반응식
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12.[CH2:21]([Mg]Br)[CH3:22].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:7]([CH:8]([OH:9])[CH2:21][CH3:22])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:12][C:3]=12

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 866767394-Chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeHCID 178420660HCID 178420660, 화합물

생성물 1

HCID 712584341-(4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-1-ol수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (117 mg, 0.360 mmol) in tetrahydrofuran (2 mL) was mixed with ethylmagnesium bromide-tetrahydrofuran solution (1.0 M, 1.0 mL, 1.0 mmol) under cooling with ice and stirred at room temperature for one day. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 (v/v)) to give the title compound as a colorless oil (75.6 mg, yield 62%).

후처리

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 (v/v))

출처 및 근거

ORD 기록
ord-87b1af9629c24331b30b28c0d9f2fabc
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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