Carbon tetrabromide → Methyl 1-({5-[5-(3-chloro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-ethyl-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 {5-[5-(3-chloro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-ethyl-2-thienyl}methanol (0.17 g, 0.41 mmol) that was obtained in Example 15 (15b), carbon tetrabromide (0.18 g, 0.53 mmol), triphenylphosphine (0.14 g, 0.53 mmol), methyl 3-azetidinecarboxylate hydrochloride (93 mg, 0.62 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) as the eluent to afford the title compound (0.15 g) in a yield of 73% as a pale yellowish oily product.

Provenance & Evidence