반응 #91551

반응 방정식

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

용매

ethyl acetate

dioxane water

반응 조건

후처리

1. 1
   건조The organic layer was dried over sodium sulphate
2. 2
   농축the filtrate was concentrated in vacuo
3. 3
   기타The crude product was purified through silica
4. 4
   세척eluting with 0-40% ethyl acetate in hexane
5. 5
   농축Appropriate fractions were concentrated in vacuo

실험 절차

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%).

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