Sodium hydride → HCID 59287320, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-fluorophenol (3.44 ml, 31.41 mmol) in N-methylpyrrolidone (20 ml) at r.t., was added sodium hydride (1.34 g, 56 mmol, 60% in mineral oil) portionwise. After stirring for 20 min, 4-nitro-2-picoline N-oxide (5.6 g, 36.12 mmol) was added. The reaction mixture was heated at 180° C. for 60 min. under microwave irradiation. After cooling to r.t. the mixture was diluted with EtOAc (250 ml), washed with water (250 ml) and then extracted with additional EtOAc (2×150 ml). The combined organic extracts were dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D25 (4.36 g, 47%).

Provenance & Evidence