4-Bromo-3-nitro-2-pyridinamine

2-Amino-3-nitro-4-bromopyridine (142 mg, 0.82 mmol)Dissolved in 3 ml of N, N-dimethylformamide/water = 10:1In a mixed solvent, Phenylboronic acid (110 mg, 0.9 mmol) was added sequentially under a nitrogen atmosphere.1, 1'-bis(diphenylphosphino)ferrocene palladium chloride (30 mg, 0.041 mmol), Potassium carbonate (339 mg, 2.46 mmol).The reaction solution was warmed to 100 C and stirred at this temperature for 3 hours.Pour the reaction solution into 20 g of ice water.Extracted with ethyl acetate (30 mL×3), The extract was washed with brine and dried over anhydrous sodium sulfate.Concentrated to a crude product.The crude product was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate = 4:1)2-amino-3-nitro-4-phenoxypyridine(87 mg, yield 45.9%).2-Amino-3-nitro-4-bromopyridine (300 mg, 1.38 mmol)Dissolved in 15 ml of anhydrous methanol and added sodium methoxide (149 mg, 2.75 mmol) under nitrogen.The reaction solution was warmed to reflux and stirred at this temperature for 1 hour.The reaction solution was concentrated to dryness and then added with 10 ml of sodium hydrogen carbonate solution.Extracted with ethyl acetate (30 mL×3), and the extract was washed with brine.Dry over anhydrous sodium sulfate and concentrate to give a crude material. Crude silica gel column chromatography(Petroleic ether / ethyl acetate = 4:1) gave 2-amino-3-nitro-4-methoxypyridine(202 mg, yield 86.5%).2-Amino-3-nitro-4-bromopyridine (1 g, 4.59 mmol)Dissolved in 20 ml of 95% ethanol, added stannous chloride(2.61 g, 13.76 mmol).The reaction solution was warmed to reflux and stirred at this temperature for 2-3 hours.Pour the reaction solution into 80 ml of 1N sodium hydroxide solution.Extracted with ethyl acetate (30 mL×3), and the extract was washed with brine.Dry over anhydrous sodium sulfate, Concentrated to a crude product.The crude product was subjected to silica gel column chromatography ( petroleum ether / ethyl acetate = 5:1)2, 3-diamino-4-bromopyridine(322 mg, yield 37%)2-Nitroamino-4-bromopyridine (3 g, 13.76 mmol) at 0 C with stirringAdd in batches to 30 ml of concentrated sulfuric acid, Slowly rise to 40 C and stir for 1 hour.Pour the reaction solution into 200 g of ice water and adjust the pH to 8-9 with concentrated ammonia water.The resulting yellow solid was filtered.The yellow solid was chromatographed on silica gel (dichloromethane / methanol = 100:1)

Molecular Weight:218.01
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:216.94869
Monoisotopic Mass:216.94869
Topological Polar Surface Area:84.7
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes