Cesium carbonate → Methyl 6-(6-Chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)nicotinate

Participants

Reaction Conditions

Reaction Steps

Methy 6-aminonicotinate (2 g, 13.1 mmol, Eq: 1.00), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (2.94 g, 13.1 mmol, Eq: 1), and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis-(diphenylphosphine) (400 mg, 691 μmol, Eq: 0.0526) were dissolved in DMF (300 ml) under heating. Cesium carbonate (12.8 g, 39.4 mmol, Eq: 3) was added followed by Pd2(dba)3 (301 mg, 329 μmol, Eq: 0.025) under an argon atmosphere. The reaction mixture was heated to 105° C. over night. The crude reaction mixture was poured into water (400 ml) and the resulting precipitate was filtered off and washed with water. The resultant filter cake was dissolved in dichloromethane. The organic phase was washed with brine, dried over sodium sulfate; filtered and concentrated to give the desired product as an off-white solid (1.523 g).

Provenance & Evidence