Sodium hydride → HCID 178516757, compound

Participants

Reaction Conditions

Reaction Steps

DMF was stirred for 10 min while being degassed with dry N2. 3-(3-bromo-4-fluorophenyl)-4,5-dihydro-1,2,4-triazin-6(1H)-one (200 mg 0.74 mmol) was then added and the mixture was degassed an additional 5 min. NaH (21 mg. 0.88 mmol) was added and the solution turned yellow; the solution was purged continuously with N2, then 2-chloro-5-chloromethypyridine (143 mg. 0.88 mmol) was added. The flask was covered with aluminum foil and stirred at approximately 25° C. for approximately 48 hours. TLC indicated a mixture of the desired product and three other components. The reaction mixture was poured into 20 mL water and 30 mL EtOAc, extracted 2× with EtOAc and the combined organics were washed with brine, dried over MgSO4, filtered and evaporated. The crude residue was purified via flash column (50% EtOAc/Hex) and evaporation of the product fractions gave ˜165 mg of material which (by NMR) appeared to be a mixture of the materials shown below.

Provenance & Evidence