Water → HCID 59354925, compound

Participants

Reaction Steps

Sodium hydride (0.022 g, 0.55 mmol) was added to a solution of cyclopentanethiol (0.053 mL, 0.50 mmol) in N,N-dimethylformamide (0.7 mL). The reaction mixture was stirred under an atmosphere of nitrogen for 5 min. Ethyl 6-chloronicotinate (0.093 g, 0.5 mmol) was added, and the reaction mixture was stirred at ambient temp over night. Water and ethyl acetate were added, and the organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography using a gradient of ethyl acetate in heptane yielded a colourless oil. The crude was dissolved in N,N-dimethylformamide (1.7 mL) and added m-chloroperbenzoic acid (60%, 171 mg, 0.59 mmol. The reaction mixture was stirred at ambient temperature under nitrogen over night. The solvent was evaporated, and the residue was partitioned between 1 M sodium hydroxide and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The formed intermediate was reduced to the title compound as described for Intermediate example I-97 yielding 58 mg (46%); 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (d, 1 H), 8.58 (dd, 1 H), 8.18 (d, 1 H), 4.04-4.15 (m, 1 H), 1.79-1.93 (m, 4 H), 1.52-1.72 (m, 4 H); MS (APPI/APCI) m/z 256[M+H+].

Provenance & Evidence