1-Ethynyl-4-(methanesulfonyl)benzene → (4-{3-[3-(4-Methanesulfonyl-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-ethynyl-4-methanesulfonyl-benzene (346 mg, 1.92 mmol), (4-{3-[3-bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester (123 mg, 0.24 mmol, example 6), Pd(PPh3)2Cl2 (17 mg, 0.024 mmol), CuI (12 mg, 0.067 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 1 hour at 65° 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-methanesulfonyl-phenylethynyl)-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 50 mg (34%) yield.

Provenance & Evidence