Sodium hydride → HCID 53374913, compound

Participants

Reaction Steps

A solution of N-(3-chlorophenyl)-3-fluoro-N′-hydroxypicolinimidamide, 3, (7.73 mmol) in DMF (50 mL) was added at 0° C. to a mixture of NaH (1.2 g, 31 mmol, 60% oil dispersion) in DMF (20 mL). After addition was complete, the ice bath was removed. An additional 12 h passed and the r×n was added to EtOAc:H2CO (1:1). The organic layer was separated and washed with H2CO, brine, dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the residue was purified by reverse phase liquid column chromatography (50-75% acetonitrile: water with 0.1% trifluoroacetic acid) to yield N-(3-chlorophenyl)isoxazolo[4,5-b]pyridin-3-amine as a pale yellow solid (0.52 g, 24% over two steps).

Provenance & Evidence