Potassium Carbonate → HCID 10470894, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloromethylpyridine hydrochloride (57.0 mg, 0.34 mmol) was combined with 50 mg of 4-methyl-mercaptopyridone intermediate (prepared analogous to Example 1) (0.22 mmol), and potassium carbonate (95.0 mg, 0.68 mmol) in DMF (1.0 mL) in a flame-dried pressure tube, under Ar. The tube was sealed and heated at 70° C. for 45 min. TLC showed complete disappearance of starting material and a new spot formed. The reaction was cooled to 0° C., and sodium hydride (9.0 mg, 0.23 mmol) was added. The reaction was warmed to room temperature and stirred for 30 min, after which it was cooled in an ice bath and quenched with aqueous sodium bicarbonate (saturated). The resulting mixture was extracted twice with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 65.8 mg of the crude product which was purified via automated flash silica to afford 41.8 mg (0.13 mmol, 59% yield) of the title compound.

Provenance & Evidence