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

HRID 705940Notes

Reaction equation

HRID 705940 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-ef074c0a61554bb093b75604f85670c2
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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