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Benzyl Bromide → 3-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indole

HRID 1297366
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HRID 1297366 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]([CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH:17]=1)[CH3:14])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.O>[CH2:3]([O:10][C:11]([N:13]([CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:17]=1)[CH3:14])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydride2회HCID 221390863-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole

생성물 1

HCID 221390153-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indole수율 93.6%

시약·촉매·용매 2

HCID 962Water용매
HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

NaH (60% dispersion in mineral oil, 0.15 g, 3.8 mmole) was added portionwise, allowing for gas evolution, to a solution of 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1H-indole (0.7 g, 2.5 mmole) in DMF (25 mL) at 0° C. When the NaH addition was complete, benzyl bromide (1.2 mL, 10.0 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over Na2SO4 and concentrated. Flash chromatography on silica gel (33% ethyl acetate/hexanes) gave the title compound (0.9 g, 93%) as an off white solid: MS (ES) m/e 385 (M+H)+.

후처리

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e42abafa13ee49248f588d64f1584974
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07250424B2

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