Sodium Bicarbonate → HCID 66777011, compound

Participants

Reaction Steps

To a mixture of cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methanone (3.00 g) synthesized above, methyl 6-aminopyridine-3-carboxylate (1.93 g), triethylamine (12.8 mL) and methylene chloride (40 mL) was added a 1.0M solution (13.8 mL) of titanium (IV) chloride in methylene chloride at 0° C., and the mixture was stirred under an argon atmosphere at room temperature for 1.5 days. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, methylene chloride was removed by an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. To a mixture of the obtained oil, ethanol (40 mL) and tetrahydrofuran (20 mL) were added acetic acid (3.29 mL) and sodium cyanoborohydride (3.61 g), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, the organic solvent was removed by an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane) to give the title object compound (547 mg, 12%) as a pale-brown solid.

Provenance & Evidence