反应详情

温度

110 °C

350 mg of 2-[2-(amino-4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (compound 4) are dissolved in 5.6 ml of anoxic dioxane under a nitrogen atmosphere. Subsequently, 3.15 ml of an aqueous sodium bicarbonate solution (2.0 M), 193 mg of 2-phenyl-1,3,2-dioxaborinane, and 49 mg of trans-dichloro-bis(tricyclohexylphosphane)palladium-(II) are added. The reaction mixture is refluxed at 110° C. for 46 hours. Thereafter, the volatile components are removed in vacuo and the remaining residue is redissolved in 200 ml of a mixture of water/dichloromethane (1:1). The aqueous phase is extracted twice each with 125 ml of dichloromethane. The organic layer is separated, dried using sodium sulfate, and evaporated to dryness to yield a colorless, crude solid. Subsequently, the residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 8:1) to afford 279 mg of the title compound as a colorless solid of m.p. 230° C. MS: 330.3 (MH+). TLC: Rf=0.34 (dichloromethane/methanol 8:1).

1. customThereafter, the volatile components are removed in vacuo
2. dissolutionthe remaining residue is redissolved in 200 ml of a mixture of water/dichloromethane (1:1)
3. extractionThe aqueous phase is extracted twice each with 125 ml of dichloromethane
4. customThe organic layer is separated
5. customdried
6. customevaporated to dryness
7. customto yield a colorless, crude solid
8. customSubsequently, the residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 8:1)