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

HRID 474702Notes

Reaction equation

HRID 474702 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

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

Workup

  1. customPurification via flash chromatography

Sources & evidence

ORD record
ord-5809aec56ec54ed1bb4c66a95ca98280
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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