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

Participants

Role	Name	HCID	Charge
Reactant	Indole	HCID 798	—
Reactant	Methyl Acrylate	HCID 7294	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Solvent	Acetonitrile	HCID 6342	—
Product	Methyl 3-(1H-indol-1-yl)propanoate	HCID 5150745	43.3%

Reaction Conditions

Temperature	50 °C

Reaction Steps

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

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09174968B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-ef074c0a61554bb093b75604f85670c2
Source note	uspto-grants-2015_11