Ammonium Chloride → (E)-tert-Butyl 5-(8-morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)picolinate

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Reaction Steps

To a solution of compound 58a (218 mg, 0.771 mmol) in 3 mL of THF at rt was added n-BuLi (482 μL, 0.771 mmol, 1.6M in hexane) dropwise. After stirring at rt for 15 min, the mixture was added slowly to a suspension of compound 61a (263 mg, 0.642 mmol) in 5 mL of THF. The resulting mixture was stirred at rt for 1 h then 2 mL of saturated NH4Cl was added. The mixture was diluted with 10 mL of water, and the mixture was extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (15 mL) and dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (0:1-1:4 EtOAc-DCM) to afford compound 61b as a pale yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 9.07 (d, J=2.0 Hz, 1H), 8.25-8.31 (m, 1H), 8.17-8.25 (m, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.77 (d, J=15.6 Hz, 1H), 7.53 (d, J=15.7 Hz, 1H), 7.29-7.37 (m, 1H), 7.23-7.29 (m, 1H), 6.13 (d, J=5.9 Hz, 1H), 4.02-4.11 (m, 4H), 3.91-4.02 (m, 4H), 2.88-2.98 (m, 2H), 2.69-2.83 (m, 2H), 1.86-1.96 (m, 2H), 1.77-1.86 (m, 2H), 1.68 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C31H34N6O3, 539.3 (M+H). found 539.5.

Provenance & Evidence