3-AMINO-5-BROMOPYRIDINE-2-CARBOXAMIDE

Add NaBKStep 1: 3-Amino-5-bromo-pyridine- -carboxylic acid amideTo a 100 mL round bottom flask, Raney Nickel (2.5 g) and EtOH (150 mL) were added. To the same flask was added 5-bromo-3-nitropyridine-2-carbonitrile (5 g, 0.0219 mol). The reaction mass was stirred under hydrogen afor 14 h at ambient temperature. The catalyst was removed by filtration. The clear filtrate was evaporated to provide the crude product. The crude was subjected to column chromatography (60-120 silica gel, 30percent ethyl acetate in hexane) to provide the title compound as a light yellow solid [1.1 g, 23percent]. 1H NMR (300 MHz, DMSO-dTo a 100 mL round bottom flask, Raney Nickel (2.5 g) and ethanol (15 mL) were added. To the same flask, was added 5-bromo-3-nitropyridine-2-carbonitrile (5 g, 0.0219 mol). The reaction mass was stirred under hydrogen atmosphere for 14 hours at ambient temperature. The catalyst was removed by filtration. The clear filtrate was evaporated to provide the crude product. The crude material was subject to column chromatography (60-120 silica gel, 30percent ethyl acetate in hexane) to provide title compound as a light yellow solid (1.1 g, 23percent). 5-Bromo-2-cyano-3-nitropyridine (2.00 g, 8.77 mmol) was dissolved in dioxane (10 mL). Water (5 mL) and ammonium hydroxide (28percent NH(4) Production of 3-amino-5-bromopyridine-2-carboxamide: 5-Bromo-3-nitropyridine-2-carboxamide (400 mg, 1.63 mmol), ammonium chloride (435 mg, 8.15 mmol) and iron powder (273 mg, 4.89 mmol) were suspended in methanol (6 mL) and water (3 mL), and stirred at 100°C for 20 hours. After cooled to room temperature, this was filtered through Celite, and the Celite was washed with methanol. The mother liquid was concentrated, and the residue was dissolved in chloroform and washed with water. The organic layer was concentrated under reduced pressure to obtain the intended compound (246 mg, 70 percent).

Molecular Weight:216.04
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:214.96942
Monoisotopic Mass:214.96942
Topological Polar Surface Area:82
Heavy Atom Count:11
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes