Benzyl chloroformate → Benzyl 1H-indol-6-ylcarbamate

HRID 2361256노트

반응식

HRID 2361256 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[CH:2]1.[C:11](Cl)(=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>O1CCCC1.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1

참가 물질

7

반응물 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 2560966-AminoindoleHCID 21226206Ethyl acetate hexane

생성물 1

HCID 67994742Benzyl 1H-indol-6-ylcarbamate수율 52.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1H-indol-6-amine (1.0 g, 7.57 mmol), benzyl carbonochloridate (1.421 mL, 9.46 mmol), and potassium carbonate (1.307 g, 9.46 mmol) in tetrahydrofuran (50 mL) was stirred at room temperature for 16 hr. The mixture was diluted with ethyl acetate (150 mL) and insoluble material was removed by filtration. The filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL). The organic solution was dried over anhydrous MgSO4. The desired product (1.05 g, 3.94 mmol, 52.1% yield) was isolated as a white solid by ISCO (120 g silica gel, solid loading, 5-30% ethyl acetate/hexane).

후처리

  1. customwas removed by filtration
  2. washThe filtrate was washed sequentially with saturated NaHCO3 solution (50 mL) and brine (50 mL)
  3. dry with materialThe organic solution was dried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-0887b02b50bd46cfae99b2696a258b2d
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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