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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 380440Generated: October 27, 2026

Methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate → Methyl 3-(propan-2-yl)-1H-indole-5-carboxylate

https://huagongshe.com/reaction/380440

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoateHCID 22663311—
Catalystpalladium(II) acetateHCID 167845—
SolventAcetonitrileHCID 6342—
SolventTriethylamineHCID 8471—
ProductMethyl 3-(propan-2-yl)-1H-indole-5-carboxylateHCID 2266317879.4%

Reaction Conditions

Temperature110 °C

Reaction Steps

A solution of methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate (2.0 g, Reference Example 53) in triethylamine (1.6 ml) and acetonitrile (35 ml) was treated with palladium acetate (0.05 g). The mixture was sealed in a bomb and heated at 110° C. for 18 hours. After cooling the reaction mixture was filtered and the filtrate was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:4, v/v) to give the title compound (1.0 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06303600B1
Source datasetuspto-grants-2001_10
ORD IDord-74d097386dd44c39b63c3883741f2ca2
Source noteuspto-grants-2001_10