2-Chloro-5-iodo-3-nitropyridine

A suspension of XIII-2 (15 g, 56.4 mmol, 1 eq.) in 35 mL of phenyl dichlorophosphate was heated at 180° C. for 30 minutes whereby a brown solution was obtained. TLC analysis (PE:EA=10:1) showed the reaction completed. The solution was allowed to cool then poured onto ice/water, neutralized by a portionwise addition of solid NaHCOA suspension of XIII-2 (15 g, 56.4 mmol, 1 eq.) in 35 mL of phenyl dichlorophosphate was heated at 180°C for 30 minutes whereby a brown solution was obtained. TLC analysis (PE:EA=10:1) showed the reaction completed. The solution was allowed to cool then poured onto ice/water, neutralized by a portionwise addition of solid NaHCO3 and extracted with ethyl acetate (150 mLx3), and then washed with aq. NaHCO3 (5percent, 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give brown solid. The crude product was purified by flash chromatography on silica gel with petroleum ether/EtOAc (5: 1—*2: 1) to give XIII-3 as yellow solid (14 g, 87percent yield). MS (ESI) m/z (M+H) 284.7.b) 2-Chloro-5-iodo-3-nitropyridineTo a solution of 5-iodo-3-nitropyridin-2-amine (1.3 g, 4.9 mmol) in concentrated HCl at 0 °C was added sodium nitrite (6.73 g, 97.13 mmol, 20 eq.) stepwise followed by the addition of copper(I) chloride (0.5 g, 4.9 mmol, 1 eq.) and the mixture was stirred at RT for 12 h. The mixture was then poured in to a mixture of ammonium hydroxide and water (1 :1) and extracted with ethylacetate (3 x 150 ml). The combined organic layer was washed with water, aqueous sodium thiosulfate, brine and dried over sodium sulphate. The solvent was distilled off to afford the product in 43 percent yield (0.6 g).To a solution of 5-iodo-3-nitropyridin-2-amine (1.3 g, 4.9 mmol) in concentrated HCl at 0° C. was added sodium nitrite (6.73 g, 97.13 mmol, 20 eq.) stepwise followed by the addition of copper(I) chloride (0.5 g, 4.9 mmol, 1 eq.) and the mixture was stirred at RT for 12 h.

Molecular Weight:284.44
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Exact Mass:283.88495
Monoisotopic Mass:283.88495
Topological Polar Surface Area:58.7
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes