(Diethylamino)sulfur trifluoride → HCID 68350418, compound

Participants

Reaction Steps

DAST (0.697 mL, 5.27 mmol) was added to a solution of (3R,4R)-benzyl 4-((6-bromo-3-cyanopyrrolo[1,2-b]pyridazin-4-yl)amino)-3-hydroxy-3-methylpyrrolidine-1-carboxylate (310 mg, 0.659 mmol) in dichloromethane (10 mL) at 0° C. After 5 min at 0° C., the mixture was carefully quenched with saturated NaHCO3 (5 mL), diluted with dichloromethane (80 mL), washed with water, brine, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography, eluting with 0 to 30% ethyl acetate in hexanes, to give (3S,4R)-benzyl 4-((6-bromo-3-cyanopyrrolo[1,2-b]pyridazin-4-yl)amino)-3-fluoro-3-methylpyrrolidine-1-carboxylate (120 mg, 39% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.84 (s, 1H), 7.69 (s, 1H), 7.48-7.31 (m, 5H), 6.77 (d, J=8.8 Hz, 1H), 5.25-5.06 (m, 2H), 4.91-4.70 (m, 1H), 4.37-4.21 (m, 1H), 3.99-3.82 (m, 1H), 3.69-3.35 (m, 2H), 1.73-1.55 (m, 3H); MS (ES+) m/z: 472.2 (M+H).

Provenance & Evidence