Benzyl Bromide → ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate

HRID 16635

반응식

HRID 16635 반응식
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH3:17])=[O:7])[CH3:4].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[CH2:18]([N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])=[C:9]1[CH3:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate

생성물 1

HCID 12701074ethyl 1-benzyl-2-methyl-1H-indole-3-carboxylate수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

General Procedure 11.-To a mixture of sodium hydride (0.28 g, 60% in mineral oil, 0.17g, 7.0 mmol) in 10 ml of tetrahydrofuran stirring at 0° C. under argon, was added 2-methyl-1H-indole-3-carboxylic acid ethyl ester (1.17 g, 5.8 mmol) and the solution was stirred at 0° C. for 15 min. Benzyl bromide (0.80 ml, 1.15 g, 6.7 mmol) was then added and the reaction allowed to warm to room temperature and stirred for 24 h. The reaction was cooled to 0° C., quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (40% EtOAc-hexanes) to yield 1-benzyl-2-methyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 57) as a tan solid (1.13 g, 67%).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 24 h
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with water
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel (40% EtOAc-hexanes)

출처 및 근거

ORD 기록
ord-b4f4de0ba9ba4ab4b09a880517932fe5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737173B2

연결된 노트

불러오는 중…