1,2-Dibromoethane → 6-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide

HRID 62663노트

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HRID 62663 반응식
[CH:1]1([NH:7][C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[C:16]([CH3:19])[CH:15]=[C:14]([OH:20])[CH:13]=3)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:27][CH2:28][CH2:29]Br>C(#N)C.O>[Br:27][CH2:28][CH2:29][O:20][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:10]([C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:9])[NH:11]2)=[C:16]([CH3:19])[CH:15]=1

참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 89995412N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide

생성물 1

HCID 899954026-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide수율 21%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a stirred solution of N-cyclohexyl-6-hydroxy-4-methyl-1H-indole-2-carboxamide (I-9A-b: 0.7 g, 2.57 mmol) in acetonitrile (20 mL) was added Cs2CO3 (1.67 g, 5.14 mmol) cooled to 0° C. followed by 1,2-dibromoethane (1.1 mL, 12.86 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 h, diluted with water (20 mL) and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate layers were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 50% ethyl acetate in petroleum ether as eluent to afford 200 mg (21%) of 6-(2-bromoethoxy)-N-cyclohexyl-4-methyl-1H-indole-2-carboxamide (I-9A-c) as an off-white solid.

후처리

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined ethyl acetate layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

출처 및 근거

ORD 기록
ord-03f5978e40894be6a0f196790dd988c2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447039B2

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