Sodium Carbonate → 6-(2-fluorophenyl)pyridazin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloropyridazin-3-amine (3.00 g, 23.1 mmol), 4-fluorophenylboronic acid (34.7 mmol), Na2CO3 (69.3 mmol) in 2-propanol (150 mL) and water (50 mL) that has been degassed with N2 (5 minutes) is added PdCl2(PPh3)2(1.15 mmol). The mixture is heated at 80° C. for 12 hours, concentrated under reduced pressure, added sat. aqueous NaHCO3 (100 mL) and extracted with EtOAc (3×100 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography using a gradient of CH2Cl2 to 70% CH2Cl2:EtOAc:methanol (1:1:0.1) to afford the title compound (3.82 g, 87%) as a white solid: Rf 0.37 (1:1:0.1 CH2Cl2:EtOAc:methanol); LCMS (m/z)=190.2 [M+H]+, tR=0.44 min.

Provenance & Evidence