Reaction #91551

Reaction equation

water

2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine

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

cesium carbonate

→

title compound

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

Solvents

ethyl acetate

dioxane water

Conditions

Workup

1. 1
   DryingThe organic layer was dried over sodium sulphate
2. 2
   Concentrationthe filtrate was concentrated in vacuo
3. 3
   OtherThe crude product was purified through silica
4. 4
   Washeluting with 0-40% ethyl acetate in hexane
5. 5
   ConcentrationAppropriate fractions were concentrated in vacuo

Procedure

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%).

Source