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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1258187Generated: October 25, 2026

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

https://huagongshe.com/reaction/1258187

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantCesium acetateHCID 5152919—
Reactant(Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic acid methyl esterHCID 86657627—
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 58437486—

Reaction Conditions

Temperature90 °C

Reaction Steps

To a solution of (Z)-3-(5-benzyloxy-2-bromo-4-methylphenyl)-2-benzyloxy-carbonylaminoacrylic 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 numberUS08466152B2
Source datasetuspto-grants-2013_06
ORD IDord-195a60ee40e64c0ea3151fd016263c1d
Source noteuspto-grants-2013_06