Water → 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine (2.83 g), 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.54 g) and cesium carbonate (9.9 g) in dioxane:water (4:1, 40 ml) was added PdCl2.dppf (0.828 g). The reaction mixture was heated at 120° C. overnight. The reaction mixture was added to water and extraction was carried out with ethyl acetate. The organic layer was dried over sodium sulphate and the filtrate was concentrated in vacuo. The crude product was purified through silica, eluting with 0-40% ethyl acetate in hexane. Appropriate fractions were concentrated in vacuo to yield the title compound, 3.8 g (84%).

Provenance & Evidence