Indole → Methyl 3-(1H-indol-1-yl)propanoate

HRID 705940노트

반응식

HRID 705940 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C1CCN2C(=NCCC2)CC1>CC#N>[N:1]1([CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 798IndoleHCID 7294Methyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 5150745Methyl 3-(1H-indol-1-yl)propanoate수율 43.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

To the solution of indole (1.20 g, 10.24 mmol) and methyl acrylate (1.384 mL, 15.37 mmol) in MeCN (20 mL) was added DBU (0.772 mL, 5.12 mmol). The mixture was heated at 50° C. overnight. Purification via flash chromatography then afforded the title compound (1.0 g, 4.43 mmol, 90% purity, 43.2% yield). LCMS: rt=3.04 min, [M+H+]=204

후처리

  1. customPurification via flash chromatography

출처 및 근거

ORD 기록
ord-ef074c0a61554bb093b75604f85670c2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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