Sodium Formate → HCID 78320808, compound

Participants

Reaction Conditions

Reaction Steps

A sealable vial was charged with N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-6-chloro-3-methylimidazo[1,2-a]pyridine-2-carboxamide (0.0513 g, 0.102 mmol, Example 6), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (7.24 mg, 10.22 μmol) and sodium formate (21 mg, 0.307 mmol, Alfa Aesar). The sealed vial was evacuated and backfilled with nitrogen. DMF (1.3 ml) was added and the reaction was stirred in a preheated 110° C. oil bath for 1 hour. The reaction was cooled to RT and partitioned between water and EtOAc. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography using a gradient of 10-100% EtOAc in hexanes to afford the title compound as a white solid. (0.0385 g, 0.082 mmol, 81% yield). MS m/z=467.9 [M+H]+. Calculated for C21H18F5N5O2: 467.39

Provenance & Evidence