Toluene → tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-3-yloxy)ethyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

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Compound 28f (97.3 mg, 0.191 mmol), 3-hydroxyquinoline (38.8 mg, 0.267 mmol), and PPh3 (70.1 mg, 0.267 mmol) were placed in an 8 mL vial equipped with a stir bar. DCM (2 mL) was added and the mixture was stirred at rt for 5 min. 40% Diethyl azodicarboxylate in toluene (0.104 mL, 0.229 mmol) was added dropwise and then the resulting solution was stirred at rt for 30 min. The crude reaction was chromatographed on a 12 g SiO2 pre-packed column and eluted with 0-80% ACN/DCM to afford compound 28g. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.59 (d, J=2.9 Hz, 1H), 8.47 (d, J=2.2 Hz, 1H), 7.95-8.05 (m, 2H), 7.84 (dd, J=8.8, 2.2 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.45-7.59 (m, 2H), 7.37 (d, J=2.7 Hz, 1H), 6.77 (d, J=8.8 Hz, 1H), 6.07 (d, J=5.6 Hz, 1H), 4.51 (t, J=6.7 Hz, 2H), 3.87-4.00 (m, 8H), 3.52-3.65 (m, 8H), 3.38 (t, J=6.7 Hz, 2H), 1.50 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C35H40N8O4: 637.3 (M+H). Found: 637.3.

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