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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1869919Generated: October 31, 2026

Triethylamine → {4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-2-fluoro-phenyl}-acetic acid methyl ester

https://huagongshe.com/reaction/1869919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantEthyl AcetateHCID 8857—
Reactant2-Fluoro-4-iodo phenyl acetic acid methyl esterHCID 18710225—
Reactant5-(Cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-4-methoxy-5,6,7,8-tetrahydro-naphthaleneHCID 21107194—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventHexaneHCID 8058—
Product{4-[5-(Cyclopropyl-methyl-amino)-4-methoxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-2-fluoro-phenyl}-acetic acid methyl esterHCID 69074012—

Reaction Steps

Following General Procedure B and using 5-(cyclopropyl-methyl-amino)-2-ethynyl-8,8-dimethyl-4-methoxy-5,6,7,8-tetrahydro-naphthalene (Intermediate 81, 0.085 g, 0.3 mmol), methyl-2-fluoro-4-iodophenylacetate (0.088 g, 0.3 mmol), triethyl amine (8 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-20% ethyl acetate in hexane as the eluent, the title compound was obtained as a yellow solid (0.12 g, 89%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07638648B2
Source datasetuspto-grants-2009_12
ORD IDord-5677e620bba343dc82f18ff8ce0143d6
Source noteuspto-grants-2009_12