Sodium borohydride → HCID 57845311, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 30 mg (0.74 mmol) of sodium borohydride in 3 mL of water was added to a solution of 0.32 g (0.68 mmol) of 1-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl}ethanone (Example 13.1) in 8 mL of EtOH and the mixture was stirred for 30 minutes at 50° C. The reaction mixture was evaporated down in vacuo, and the residue was stirred for 5 minutes with 4 mL of 1N aqueous HCl, diluted with EtOAc, and neutralized with saturated aqueous sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. The residue was triturated with acetonitrile and a little EtOAc, the precipitate was filtered off, and dried in the air. Yield: 100 mg (31% of theoretical); C29H31ClN2O2 (M=475.021); calc.: molpeak (M+H)+: 475/477 (Cl); found: molpeak (M+H)+: 475/477 (Cl); HPLC-MS: 5.20 minutes (method A).

Provenance & Evidence