Reference of 6627-78-7,Some common heterocyclic compound, 6627-78-7, name is 1-Bromo-4-methylnaphthalene, molecular formula is C11H9Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of 1-bromo-4-methylnaphthalene (1.0 g, 4.52 mmol, 1.0 eq), tert-butyl 4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-l(2H)-carboxylate (2.1 g, 6.78 mmol, 1.5 eq) and Na2C03 (1.43 g, 13.56 mmol, 3.0 eq) in a mixture of 1,2-DME (15 mL) and water (5 mL) was purged with nitrogen for 15 min. Pd(dppf)Cl2 DCM (0.36 g, 0.45 mmol, 0.1 eq) was added to the reaction mixture and was stirred under nitrogen atmosphere, at 80 C for 2 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2S04, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude product, which was purified by flash chromatography on silica gel, 230-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain tert-butyl 4-(4-methylnaphthalen-l-yl)-3,6-dihydropyridine-l(2H)-carboxylate. LCMS: Purity 82.42%. MS calculated for [M]323.44 and found [M+H] +324.20
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-methylnaphthalene, its application will become more common.
Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; PANDEY, Anjali; BOWERS, Simeon; BARTA, Thomas E.; BOURNE, Jonathan William; (208 pag.)WO2017/147328; (2017); A1;,
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