Carbon tetrabromide → Methyl 1-({4-ethyl-5-[5-(3-fluoro-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-ethyl-5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (0.16 g, 0.40 mmol) that was obtained in Example 14 (14a), carbon tetrabromide (0.17 g, 0.52 mmol), triphenylphosphine (0.14 g, 0.52 mmol), methyl 3-azetidinecarboxylate hydrochloride (91 mg, 0.60 mmol), and N,N-diisopropylethylamine (0.21 mL, 1.2 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 (1:3 to 1:2) as the eluent to afford the title compound (0.15 g) in a yield of 77% as a pale yellow oily product.

Provenance & Evidence