2-Chloro-1-methylpyridinium iodide → HCID 59408770, compound

Participants

Reaction Steps

To a suspension of 5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid 1 (400 mg, 1.37 mmol) and 2-chloro-1-methylpyridinium iodide (524 mg, 2.0 mmol) in THF (20 ml), DIPEA (0.46 ml) followed by 6-bromopyridin-2-amine 2 (237 mg, 1.37 mmol) were added. The suspension was stirred for 72 hrs. Then the reaction mixture was concentrated, diluted in water (10 ml) and extracted with dichloromethane (50 ml×2). All organic phases were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column (EtOAc: pet-ether 1:4) to give N-(6-bromopyridin-2-yl)-5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxamide 3 (180 mg) as a white solid. Mp. 151-152° C.

Provenance & Evidence