Diisopropylethylamine → HCID 59408770, compound

Participants

Reaction Steps

2-Chloro-1-methylpyridinium iodide (950 mg, 3.7 mmol) and DIPEA (0.7 mL) were added to a solution of 6-bromopicolinic acid 2 (500 mg, 2.47 mmol) in dry DCM/DMF (30/5 mL). The reaction mixture was stirred for 1 hr. tert-Butyl 3-amino-5-(4-fluorophenyl)-1H-pyrazole-1-carboxylate 1 was added (650 mg, 2.47 mmol). The resulting yellow reaction mixture was stirred for 3 days. Then the reaction mixture was concentrated under reduced pressure, the residue was diluted in chloroform and washed with water and brine, and then dried over Na2SO4. The resulting crude mixture was purified on silica gel (EtOAc: pet-ether, 1:3) to give 6-bromo-N-(5-(4-fluorophenyl)-1H-pyrazol-3-yl) picolinamide 3 (450 mg, 50%) as a white solid.

Provenance & Evidence