Potassium Fluoride → 3-Bromo-6-(2-(2,5-dimethylphenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine

Participants

Reaction Conditions

Reaction Steps

In step 4-1, potassium fluoride (58 mg, 1.0 mmol), and (3-bromo-6-chloroimidazo[1,2-b]pyridazine (12-1) (100 mg, 0.43 mmol) was added to a solution of 2-(2,5-dimethylphenyl)pyrrolidine (100 mg, 0.57 mmol) in 3 mL of DMSO. The reaction mixture was heated to 130° C. and stirred for 6 hours at 130° C. The reaction mixture was cooled to room temperature and purified using normal phase flash chromatography with ethyl acetate and hexanes (1:1) as a mobile phase to yield 3-bromo-6-(2-(2,5-dimethylphenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine (4-1) as its racemic mixture. 1H NMR (400 MHz, D3 acetonitrile) δ ppm 7.50 (app d, J=9.5 Hz, 1H), 7.40 (br s, 1H), 7.08 (d, J=6.5 Hz, 1H), 6.92 (d, J=6.6 Hz, 1H), 6.82 (br s, 1H), 6.58 (br d, J=9.5 Hz, 1H), 5.28 (br d, J=5.0 Hz, 1H), 4.08-3.95 (m, 1H), 3.62 (app q, J=6.4 Hz, 1H), 3.30 (s, 1H), 2.51-2.42 (m, 1H), 2.24 (br s, 6H), 2.17-2.04 (m, 2H). LCMS observed m/z 371.1, 373.1 major ion.

Provenance & Evidence