Ammonia → 3-Methyl-6-(trifluoromethyl)pyridazine

Participants

Reaction Steps

A mixture of CuI (263 mg) and KF (80 mg) was heated under vacuum for 30 minutes until a greenish colour was observed. The system was filled with N2 and a solution of 3-iodo-6-methylpyridazine (300 mg) in DMF (1.25 ml) and N-methylpyrrolidinone (1.25 ml) followed by trimethyl(trifluoromethyl)silane (185 μl) were subsequently added. A dark brown colour was observed. After stirring at room temperature for 5 days, the reaction was not complete. CuI (263 mg), KF (80 mg), and CF3TMS (185 μl) were added and stirring was continued overnight. Additional CuI (135 mg), KF (40 mg), and CF3TMS (90 μl) were added and after one more day at room temperature, almost no starting material was observed. Aqueous ammonia and TBME were added and the phases were separated. The aqueous one was washed with TBME. The organic extracts were combined and subsequently washed with aqueous ammonia, 1M HCl, saturated NaHCO3, and brine, dried over Na2SO4, filtered and concentrated to give 70 mg (35%) of the title compound.

Provenance & Evidence