Water → Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

HRID 2108735노트

반응식

HRID 2108735 반응식
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15][CH2:16][C:17](Br)=[O:18].O>ClCCl>[Br:15][CH2:16][C:17]([C:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[F:1])[NH:8][CH:9]=1)=[O:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 112979984-Fluoro-1H-pyrrolo(2,3-b)pyridine

생성물 1

HCID 57421973Ethanone, 2-bromo-1-(4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (2.00 g, 0.0147 mol) (Org. Lett., 2003, 5, 5023-5025) in dichloromethane was added aluminum chloride (3.92 g, 0.0294 mol) in portions, the mixture was stirred at RT for 30 min, then bromoacetyl bromide (4.45 g, 0.022 mol) was added dropwise. The reaction mixture was stirred at 50° C. for 1 h, when TLC indicated no starting material. To the reaction mixture was added 150 mL water, and the resulting suspension was heated at 100° C. for 1 h, then filtered to afford the desired product, 90% pure. H NMR, DMSO-d6: 4.72(s, 2H), 7.12(m, 1H), 8.36(m, 1H), 8.67(s, 1H).

후처리

  1. stirringThe reaction mixture was stirred at 50° C. for 1 h
  2. temperaturethe resulting suspension was heated at 100° C. for 1 h
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-f43fced1acc84e01a9a38feb9f7b5cd7
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514448B2

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