Potassium Fluoride → HCID 58335815, compound

Participants

Reaction Conditions

Reaction Steps

In step 3-4, KF (100 mg, 1.72 mmol) and 3-bromo-6-chloroimidazo[1,2-b]pyridazine (12-1) (700 mg, 3.0 mmol) were added to a solution of (3S)-2-(3-fluorophenyl)-3-(triisopropylsilyloxy)pyrrolidine (4-3) (700 g, 2.0 mmol) in 3 mL of DMSO. The resulting slurry was heated to 110° C. for 6 hours and then cooled, diluted with 8 mL of MeOH and purified using reverse phase C-18 chromatography (water/acetonitrile 90:10 to 10:90 gradient) to furnish (3S)-1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-2-(3-fluorophenyl)pyrrolidin-3-ol (3-4) as a solid (as a mixture of diastereomers). 1H NMR (400 MHz, D6 acetone) δ ppm 8.20 (app t, J=6.5 Hz, 1H), 7.85-6.70 (m, 6H), 5.05 (app d, J=5.5 Hz, 1H), 4.68 (app q, J=7.5 Hz, 1H), 4.30 (br s, 1H), 4.01-3.92 (m, 1H), 3.82-3.70 (m, 1H), 2.35-1.87 (m, 2H). LCMS observed m/z 377.1, 379.1 major ion.

Provenance & Evidence