Water → HCID 67348764, compound

Participants

Reaction Steps

Sodium hydride (added with 40% mineral oil, 13.5 mg, manufactured by Kanto Chemical Co., Inc.) was added to a solution of ethyl 2-(6-hydroxy-3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate (20 mg), which had been synthesized from the compound of Reference Example 20 according to the method of Example 3, in N,N-dimethylformamide (1 mL, manufactured by Kanto Chemical Co., Inc.) under ice cooling, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, bromocyclopentane (269 mg, manufactured by Kanto Chemical Co., Inc.) was added, and the mixture was stirred overnight at room temperature. Water (10 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether (3×10 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1), to give 6.9 mg of the title compound. LC-MS: HPLC retention time 2.13 minutes, m/z 434 (M+H), condition C-1.

Provenance & Evidence