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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1894038Generated: October 31, 2026

Triethylamine → HCID 59164526, compound

https://huagongshe.com/reaction/1894038

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant3-MethoxypropyneHCID 69393—
ReactantMethyl 2-amino-5-iodo-4-(trifluoromethyl)benzoateHCID 53436880—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 59164526HCID 5916452678%

Reaction Conditions

Temperature55 °C

Reaction Steps

A solution of 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (3.0 g, 8.69 mmol) and Et3N (22 mL) in dry dioxane (22 mL) was purged with argon during 15 min. (Ph3P)2PdCl2 (305 mg, 0.435 mmol), CuI (166 mg) and 3-methoxy-propyne (2.20 mL, 26.08 mmol) were added and the mixture was heated to 55° C. for 100 min. After cooling, the reaction mixture was filtered and the filtrate diluted with EtOAc, washed with water and brine and dried (Na2SO4). Evaporation of the volatiles gave a residue which was purified by MPLC (silica gel, cyclohexane/EtOAc 4:1) to yield the title compound (1.94 g, 78%) as a beige solid, m.p. 107-111° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08513268B2
Source datasetuspto-grants-2013_08
ORD IDord-ae7af35feadc4f348f6981883933a07f
Source noteuspto-grants-2013_08