Diisobutylaluminum hydride → HCID 86696434, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of PdCl2dppf (25 mg, 0.03 mmol) and (S)-tert-butyl 2-(((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)methyl)pyrrolidine-1-carboxylate (100 mg, 0.2 mmol) in dioxane (2 mL) was added diethylzinc (0.24 ml, 1 M in hexane), DiBAL-H (0.008 mL, 1M in toluene) at room temperature. The reaction mixture was heated to 100° C. and stirred for 2 h. Filtered off celite, and concentrated the filtrate, purified by Prep HPLC (neutral) to give (S)-tert-butyl 2-(((3-ethylimidazo[1,2-b]pyridazin-6-yl)amino)methyl)pyrrolidine-1-carboxylate as oil. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.55 (d, J=9.60 Hz, 1H), 7.22 (s, 1H), 6.66 (d, J=9.60 Hz, 1H), 4.18 (br. s., 1H), 3.55 (br. s., 1H), 3.37-3.49 (m, 3H), 2.91 (q, J=7.49 Hz, 2H), 1.87-2.07 (m, 4H), 1.44 (br. s., 9H), 1.36 (t, J=7.45 Hz, 3H); LRMS (ESI) m/e 346.3 [(M+H)+, calcd for C18H28N6O2 346.4.

Provenance & Evidence