Cesium carbonate → 5-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 1790893

반응식

HRID 1790893 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].Cl[CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:17][C:18](=[O:19])[N:20]([CH3:22])[CH3:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

생성물 1

HCID 695870655-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester수율 48.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-hydroxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 10 mmol), 2-chloro-N,N-dimethylacetamide (1.33 g, 11 mmol) and cesium carbonate (9.8 g, 30 mmol)) in dimethylformamide (20 mL) was stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (150 mL), washed with water (5×50 mL) and brine, dried and concentrated. The residue was recrystallized from ethyl acetate and hexane to give 1.4 g of 5-dimethylcarbamoylmethoxy-1H-indole-2-carboxylic acid ethyl ester as a brown solid.

후처리

  1. washwashed with water (5×50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-08e9eb19e15d4e6fa1eb511e4a67f7f7
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071332B2

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