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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 73330Generated: October 27, 2026

Ammonia → 5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl ester

https://huagongshe.com/reaction/73330

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantCesium acetateHCID 5152919—
Reactant(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl esterHCID 58437218—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventDimethyl SulfoxideHCID 679—
Product5-Benzyloxy-6-methyl-1H-indole-2-carboxylic acid methyl esterHCID 5843748663.1%

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of (Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxycarbonylaminoacrylic acid methyl ester (0.2 g) and copper (I) iodide (0.075 g) in dimethylsulfoxide (8 mL) was added cesium acetate (0.38 g) at room temperature and this mixture was stirred under argon atmosphere at 90° C. for 5 hours. To this reaction mixture was added aqueous ammonia solution (28%) and the precipitated solid was collected by filtration, and washed with water, dried under reduced pressure to give the title compound (0.073 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829040B2
Source datasetuspto-grants-2014_09
ORD IDord-865e985d28cb44e48a972d7c9f48d8fb
Source noteuspto-grants-2014_09