Tetrahydrofuran → HCID 131734499, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL microwave vial was charged with sodium tert-butoxide (103 mg, 1.075 mmol), methyl (6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (252 mg, 0.537 mmol), benzyl carbamate (122 mg, 0.806 mmol) and BrettPhos-G3-Pd (24.36 mg, 0.027 mmol). THF (6 ml) was added, the vial was flushed with argon, capped and the contents heated to 50° C. with stirring for 10 h. LCMS analysis indicated incomplete conversion to the desired product. Excess benzyl carbamate (61 mg), sodium tert-butoxide (51 mg) and BrettPhos-G3-Pd (12 mg) was added. The vial was flushed with argon, capped and the contents heated to 50° C. for an additional 4 h. The mixture was cooled, diluted with ethyl acetate (10 mL), washed with saturated aqueous sodium hydrogen carbonate (2×20 mL), dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (ISCO; 24 g prepacked) eluting with ethyl acetate/hexanes to afford benzyl methyl (1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diyl)dicarbamate (126 mg, 0.216 mmol, 40.2% yield) as a white solid. MS ESI calc'd. For C35H30N5O4 [M+H]+ 584. found 584.

Provenance & Evidence