Triphenylphosphine → tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 5e (0.57 g, 2.5 mmol), tert-butyl-4-bromobenzoate (0.97 g, 3.7 mmol), palladium acetate (38 mg, 0.17 mmol), triphenylphosphine (45 mg, 0.17 mmol) and potassium acetate (0.72 g, 7.3 mmol) were added while under an argon atmosphere and in dry N,N-dimethylacetamide (5 mL). The reaction mixture was stirred at 110° C. for 22 h, allowed to cool to rt, diluted with water (100 mL), and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The obtained residue was purified by flash chromatography on silica gel (10-60% EtOAc/heptane) to give compound 5f as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 10.13 (s, 1H), 8.13-8.21 (m, J=8.1 Hz, 2H), 8.09 (d, J=5.6 Hz, 1H), 7.85 (d, J=8.3 Hz, 2H), 6.15 (d, J=5.6 Hz, 1H), 4.02-4.14 (m, 4H), 3.90-4.00 (m, 4H), 1.62 (s, 9H).

Provenance & Evidence