Hydrochloric Acid → HCID 58221582, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred ice-cooled solution of 6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran] (0.7 g, 2.46 mmol), 4-dimethylaminopyridine (0.03 g, 0.25 mmol) and Et3N (0.37 g, 3.69 mmol) in DCM (25 mL) was added acetyl chloride (0.21 mL, 2.96 mmol) via syringe. The resulting mixture was stirred at 0° C. for 5 min and at rt for 1.5 h. After this time the mixture was poured into ice and 2N aqueous HCl and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, saturated aqueous NaHCO3, brine, and dried over anhydrous Na2SO4. Purification by column chromatography (EtOAc:hexanes) gave 1-acetyl-6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran] as an off-white solid. Mass Spectrum (ESI) m/e=326.0 [(M+1) (79Br)] and 328.0 [(M+1) (81Br)].

Provenance & Evidence