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Chloroacetyl chloride → 1-(5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-chloro-ethanone

HRID 85091
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HRID 85091 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([CH3:15])[NH:12][C:9]2=[N:10][CH:11]=1.[Cl:16][CH2:17][C:18](Cl)=[O:19]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:14]([C:18](=[O:19])[CH2:17][Cl:16])=[C:13]([CH3:15])[NH:12][C:9]2=[N:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 454896915-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 866916661-(5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-chloro-ethanone수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of AlCl3 (1.57 g, 11.84 mmol) in dichloromethane (50 mL) was added 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine. After stirring for 30 min, chloroacetyl chloride (1.33 g, 11.84 mmol) was added and the reaction mixture was stirred for 2 hours at room temperature. On completion, solvents were evaporated and quenched with aq. NaHCO3 solution at 0° C. Resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered through a plug of silica gel. Solvent was evaporated to dryness to give 1-(5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-chloro-ethanone (0.650 g, 95% yield).

후처리

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. customOn completion, solvents were evaporated
  3. customquenched with aq. NaHCO3 solution at 0° C
  4. customResulting mixture
  5. extractionwas extracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated to dryness

출처 및 근거

ORD 기록
ord-d73147c946b9437fbb94cd2fa37ea539
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846909B2

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