Carbon tetrabromide → Methyl 1-({4-methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methyl)azetidine-3-carboxylate

Participants

Reaction Steps

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using {4-methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (0.19 g, 0.51 mmol) that was obtained in Example 12 (12a), carbon tetrabromide (0.22 g, 0.66 mmol), triphenylphosphine (0.17 g, 0.66 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.12 g, 0.77 mmol), and N,N-diisopropylethylamine (0.27 mL, 1.5 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (2:3) as the eluent to afford the title compound (0.20 g) in a yield of 85% as a pale yellowish oily product.

Provenance & Evidence