Ethyl 4,6-dichloropyridazine-3-carboxylate → Ethyl 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (674 mg, 3.05 mmol) in acetonitrile (10 mL) was added 5-fluoro-6-isopropylpyridin-2-amine (470 mg, 3.05 mmol) and heated at 130° C. in a sealed tube for 18 h. Upon completion, the mixture was concentrated on to silica gel and purified by chromatography (silica. 10% to 33% EtOAc in hexanes) to give recovered aniline (300 mg) and ethyl 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (150 mg, 22%). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 10.72 (s, 1H), 9.23 (s, 1H), 7.38 (t, J=8.4 Hz, 1H), 6.79 (dd, J=8.5, 2.8 Hz, 1H), 4.57 (m, 2H), 3.45 (m, 1H), 1.53 (m, 3H), 1.36 (d, J=6.9 Hz, 6H).

Provenance & Evidence