3-Amino-2-chloro-6-iodopyridine

Step a: 6-chloropyridin-3-amine (40.0 g, 311 mmol) was dissolved in DMF (Volume: 534 mL) and treated with 1-iodopyrrolidine-2, 5-dione (70.0 g, 311 mmol) in one portion. The reaction solution was stirred at room temperature under nitrogen overnight and quenched with water and extracted with EtOAc and Et6-chloropyridin-3-amine (40.0 g, 311 mmol) was dissolved in dimethylformamide (DMF) (Volume: 534 mL) and treated with 1-iodopyrrolidine-2, 5-dione (70.0 g, 311 mmol) in one portion. The reaction solution was stirred at room temperature under nitrogen overnight and quenched with water and extracted with EtOAc and EtPREPARATION 17 6-Chloro-2-iodopyridin-3 -amine 6-Chloropyridin-3-amine (3.00 g, 23.3 mmol) was dissolved in 40 ml dimethyl- formamide. /V-lodosuccinimide (5.25 g, 23.3 mmol) was added and the mixture was stirred at room temperature for 16 h. Further /V-iodosuccinimide (1 .79 g, 7.9 mmol) was added and stirring was continued for 4 h. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate-hexane, 20:80) to yield 4.03 g of the title compound (15.8 mmol, 68percent) as a beige solid. Purity 95percent.   6-Chloropyridin-3-amine (3.00 g, 23.3 mmol) was dissolved in 40 ml dimethylformamide. N-lodosuccinimide (5.25 g, 23.3 mmol) was added and the mixture was stirred at room temperature for 16 h. Further N-iodosuccinimide (1.79 g, 7.9 mmol) was added and stirring was continued for 4 h. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate-hexane, 20:80) to yield 4.03 g of the title compound (15.8 mmol, 68percent) as a beige solid. Purity 95percent. [0276] N-lodosuccinimide (5.25 g, 20 mmol) was added to a solution of 6-chloropyridin-3-amine (2.5 g, 20 mmol) in 40 ml N, N-dimethylformamide and the mixture was stirred overnight at room temperature. The reaction mixture was partitioned between water and ethyl acetate and organic layer was washed with brine, dried (MgSOPREPARATION I

Molecular Weight:254.45
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:253.91077
Monoisotopic Mass:253.91077
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:101
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes