Chlorotrimethylsilane → (E)-tert-Butyl 4-(2-(2-(3-methoxyquinolin-2-yl)vinyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

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Reaction Conditions

Reaction Steps

To a mixture of compound 5f (100 mg, 0.245 mmol) and 3-methoxy-2-methylquinoline (212 mg, 1.22 mmol) in 4 mL of DMF was added TMSCl (312 μL, 2.45 mmol) dropwise. The resulting mixture was stirred at 90° C. for 24 h. After cooling to rt, the mixture was treated with 60 mL of EtOAc and washed with water (3×20 mL), brine (15 mL) and then dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (0:1-1:9 EtOAc/DCM) to afford compound 63a as a yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 8.10-8.25 (m, 4H), 7.99 (d, J=5.9 Hz, 2H), 7.86 (d, J=8.3 Hz, 2H), 7.68 (d, J=8.1 Hz, 1H), 7.49-7.55 (m, 1H), 7.39-7.47 (m, 1H), 7.37 (s, 1H), 6.11 (d, J=5.6 Hz, 1H), 4.04-4.12 (m, 4H), 3.96-4.04 (m, 4H), 4.01 (s, 3H), 1.64 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C33H33N5O4, 564.3 (M+H). found 564.5.

Provenance & Evidence