4-(2-Propyn-1-yl)morpholine → (4-{3-[3-Bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-prop-2-ynyl-morpholine (330 mg, 2.64 mmol), {4-[3-(3,5-dibromophenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester (206 mg, 0.44 mmol, intermediate 2), Pd(PPh3)2Cl2 (50 mg, 0.044 mmol), CuI (23 mg, 0.123 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 30 min at 60° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using methylene chloride/THF mixtures to give (4-{3-[3-bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid methyl ester in 130 mg (58%) yield.

Provenance & Evidence