3,6-Dichloropyridazine → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)difluoromethyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,2-difluoro-2-(quinolin-6-yl)acetohydrazide (2000 mg, 8432 μmol) and 3,6-dichloropyridazine (3768 mg, 25295 μmol) in 1.25 M HCl in MeOH (20 mL) was heated to 90° C. with microwaves for 50 min. The solvents were then removed under reduced pressure and residue partitioned between 9:1 CHCl3/IPA (60 mL) and 1 M NaOH (20 mL). The organic phase then dried over MgSO4, concentrated, then purified on silica (120 g) eluting with 1>2.5% of 2 M NH3 in MeOH/DCM to provide product isolated as a dark tan solid. MS (ESI pos. ion) m/z: 332 (MH+). Calc'd exact mass for C15H8ClF2N5: 331.

Provenance & Evidence