8-Bromo-1,7-naphthyridin-6-amine

(3) 8-bromo-l, 7-naphthyridin-6-amine.; To a 50 mL round-bottomed flask was added hydrobromic acid, 30percent in acetic acid (317 μl, 5868 μmol). 3-(cyanomethyl)picolinonitrile (280 mg, 1956 μmol) in AcOH (0.5 mL) was then added at 0 (3) 8-bromo-l, 7-naphthyridin-6-amine.; To a 50 mL round-bottomed flask was added hydrobromic acid, 30% in acetic acid (317 mul, 5868 mumol). 3-(cyanomethyl)picolinonitrile (280 mg, 1956 mumol) in AcOH (0.5 mL) was then added at 0 0C. The reaction mixture was stirred at 0 0C for 30 min. The solid was filtered out and washed with 50% EtOAc/hexanes. The solid was treated with sat. NaHCO3 (5 mL) and the mixture was extracted with EtOAc (2 x 50 mL). The organic extract was washed with satd NaCl (5 mL), dried over Na2SO4, filtered and B. 6-Amino-8-bromo-1, 7-naphthyridine Through a stirred solution of 2-Cyano-3-pyridylacetonitrile (3.6 g, 0.025 mol) in toluene (80 ml) is bubbled HBr for 5 h. Then, 4N NaOH is carefully added and the suspension stirred vigorously. The mixture is filtered and the product washed with water and dried. Crystallisation from toluene affords the title compound. Mass M+H 225. Melting point 188 C., decomposition.To a mixture of THF (80 ml) and 2N sodium carbonate (34 ml, aqueous) is added 6-amino- 8-BROM-1, 7-naphthyridine (4.007 g), triphenylphosphine (0.37 g) and 3-cyanophenyl- boronic acid (3.23 g). The mixture is degassed under argon three times and then bis (di- benzylidene-acetone) palladium (0) (0.4 g) is added and the mixture is degassed under argon three more times. The mixture is heated at 80C under argon for 16 hours then cooled and filtered. The mixture is diluted with ethyl acetate and washed with 2N sodium hydroxide then brine. After drying over sodium sulfate the organic layer is evaporated and suspended in ether. The solid precipitate thus obtained is the title compound, which is filtered off.

Molecular Weight:224.06
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:222.97451
Monoisotopic Mass:222.97451
Topological Polar Surface Area:51.8
Heavy Atom Count:12
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes