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A mixture of Example 13B (18g, 163.44mmol) and phosphorus oxybromide (93.8g, 327.6mmol) was stirred at70°C overnight. The mixture was cooled to 40°C, poured into ice-water, quenched with saturated sodium bicarbonate(20mL) and extracted with dichloromethane (100mL 3 3). The organic layers were combined, dried over anhydroussodium sulfate, filtered and evaporated to give the title compound, 3-bromo-6-methylpyridazine (8g, yield 31percent). LCMS(ESI) m/z: 173[M+1]+. 1H NMR (CHLOROFORM-d, BrukerAvance 400MHz): ppm 7.86-7.88 (d, 1H, J = 8 Hz), 7.52-7.54(d, 1H, J = 8 Hz), 2.55(s, 3H).
A mixture of Example 13B (18g, 163.44mmol) and phosphorus oxybromide (93.8g, 327.6mmol) was stirred at70C overnight. The mixture was cooled to 40C, poured into ice-water, quenched with saturated sodium bicarbonate(20mL) and extracted with dichloromethane (100mL 3 3). The organic layers were combined, dried over anhydroussodium sulfate, filtered and evaporated to give the title compound, 3-bromo-6-methylpyridazine (8g, yield 31%). LCMS(ESI) m/z: 173[M+1]+. 1H NMR (CHLOROFORM-d, BrukerAvance 400MHz): ppm 7.86-7.88 (d, 1H, J = 8 Hz), 7.52-7.54(d, 1H, J = 8 Hz), 2.55(s, 3H).
6-Methylpyridazin-3(2H)-one (Alfa, 2.5 g, 22.70 mmol) and phosphorus oxybromide (Aldrich, 16.27 g, 56.8 mmol) were heated at 90 C under a nitrogen atmosphere for 1.5 hours. After cooling, the mixture was poured onto ice (100 g), neutralized with sodium bicarbonate, and the aqueous phase was extracted with CH2Cl2 (3chi30 mL). The combined organic phase was washed with 5% NaHCO3, brine, dried (Na2SO4) and concentrated. The residue was dissolved in hot ethyl acetate and washed through a plug of silica gel, eluting with ethyl acetate and concentrated. MS (DCI/NH3) m/z 172 (M+H)+, 190 (M+NH4)+.
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