Propyne → HCID 69343046, compound

Participants

Reaction Steps

Propyne (excess ca 3 ml) was condensed onto a cold (−78° C.) solution of 2-amino-5-chloro-3-iodobenzoic acid methyl ester (500 mg, 1.61 mmol) in triethylamine (10 ml) in a Parr pressure reaction vessel. To this solution was added copper (I) iodide and bis(triphenylphosphine)palladium (II) chloride and the pressure tube was then sealed and stirred at rt for 4 h. The solvent was then removed in vacuo and the residue was purified by flash column chromatography (9:1 cyclohexane:EtOAc) to give 2-amino-5-chloro-3-prop-1-ynylbenzoic acid methyl ester (340 mg, 95%) as an off white solid. 1H NMR (CDCl3, 300 MHz): δ 7.76 (d, J=2.5 Hz, 1H), 7.33 (d, J=2.5 Hz, 1H), 6.37 (br s, 2H), 3.87 (s, 3H), 2.13 (s, 3H).

Provenance & Evidence