1,2-Dimethoxyethane → 4-(6-Butylamino-imidazo[1,2-b]pyridazin-3-yl)-3-fluoro-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (810 mg, 3.0 mmol), 2-fluoro-4-formylphenylboronic acid (1.2 g, 7.5 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (200 mg, 0.30 mmol), potassium phosphate (1.9 g, 9.0 mmol), DME (9 mL) and H2O (3 mL) was maintained in a sealed vessel at 80° C. for 12 h. The organic layer was separated and concentrated under reduced pressure to afford a yellow solid that was purified by reverse phase HPLC to afford 4-(6-butylamino-imidazo[1,2-b]pyridazin-3-yl)-3-fluoro-benzaldehyde (600 mg, 64%) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 10.02 (d, J=1.8 Hz, 1H), 8.84-8.93 (m, 1H), 8.12 (d, J=4.3 Hz, 1H), 7.79 (dd, J=8.1, 1.5 Hz, 1H), 7.68-7.76 (m, 2H), 6.55 (d, J=9.6 Hz, 1H), 3.43 (td, J=7.1, 5.6 Hz, 2H), 1.67-1.78 (m, 2H), 1.49 (dq, J=15.0, 7.4 Hz, 2H), 1.01 (t, J=7.3 Hz, 3H); LCMS (ESI) m/e 313.1 [(M+H)+, calcd for C17H18FN4O 313.1].

Provenance & Evidence