Sodium Hydroxide → 1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone

HRID 1515948노트

반응식

HRID 1515948 반응식
[CH3:1][CH:2]([CH3:32])[CH:3]=[C:4]([C:23]1[CH:24]=[C:25]([C:29](=[O:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1)[C:5]1[N:13](S(C2C=CC=CC=2)(=O)=O)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][CH:2]([CH3:32])[CH:3]=[C:4]([C:23]1[CH:24]=[C:25]([C:29](=[O:31])[CH3:30])[CH:26]=[CH:27][CH:28]=1)[C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 672291181-(3-(3-methyl-1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone

생성물 1

HCID 672297431-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone수율 82.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A solution of 1-(3-(3-methyl-1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone (1.5 g, 3.4 mmol) in ethanol (30 mL) and tetrahydrofuran (60 mL) was treated with an aqueous sodium hydroxide solution (10%, 20 mL). The reaction was stirred at 80° C. for 16 h. Most of the solvent was removed in vacuo. The resulting precipitate was removed by filtration and washed with water (50 mL). The filtrate was concentrated in vacuo. Silica gel column chromatography (30 g, 200-300 mesh, 15% ethyl acetate/petroleum ether) afforded 1-(3-(3-methyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)but-1-enyl)phenyl)ethanone (0.85 g, 82.2%) as an off-white solid: 1H NMR (300 MHz, d6-DMSO) δ ppm 11.60 (s, 1H), 8.20 (dd, 1H, J1=4.8 Hz, J2=1.5 Hz), 7.96 (d, 1H, J=8.1 Hz), 7.90-7.87 (m, 1H), 7.78 (s, 1H), 7.48-7.46 (m, 2H), 7.09 (dd, 1H, J1=7.5 Hz, J2=5.1 Hz), 6.44 (d, 1H, J=1.8 Hz), 6.24 (d, 1H, J=9.9 Hz), 2.63-2.56 (m, 1H), 2.57 (s, 3H), 1.08-1.02 (m, 6H).

후처리

  1. customMost of the solvent was removed in vacuo
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with water (50 mL)
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-bd15335fa6fa4bdeab93941b657cf7fc
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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