Benzene, 1-chloro-4-ethynyl- → (4-{3-[3-(4-Chloro-phenylethynyl)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-chloro-4-ethynyl-benzene (240 mg, 1.76 mmol), (4-{3-[3-bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (106 mg, 0.207 mmol, example 6), Pd(PPh3)4 (23 mg, 0.021 mmol), CuI (11 mg, 0.058 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 120 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-(4-chloro-phenylethynyl)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 63 mg (54%) yield.

Provenance & Evidence