6-Chloro-2-iodo-3-pyridinol

A solution of the above material (15.48 g, 119 mmol) and Na2CO3 (26.56 g, 251 mmol) in water (300 mL) was charged with iodine (30.3 g, 119 mmol). The reaction mixture was stirred at room temperature until the iodine color disappeared, approx. 48 h. The solution was adjusted to pH =5 with 1 N aqueous HCl, and extracted with ethyl acetate. The organic layers were washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated in vacuo. The resulting white solid was recrystallized from methanol to provide 17.8 g (95percent) of the title compound. MS(m/e): 256 (M+); Calculated for C5H3ClINO: Theory: C, 23.51; H, 1.18; N, 5.48; Found: C, 23.72; H, 1.19; N, 5.45.To a stirred solution of 2-chloro-5-hydroxypyridine (6.0 g, 46.3 mmol) in HStep 1: 6-chloro-2-iodopyridin-3-ol To solution of 6-chloro-pyridin-3-ol (112 g, 868 mmol) in THF (800 mL)/Water (800 mL) was added sodium carbonate (92.0 g, 1.736 mol;) and iodine (244.2 g, 1.04 mol;). The reaction mixture was stirred rt 4 h. The aqueous layer containing product was separated and washed with hexane (400 mL.x.2). The aqueous layer was neutralized to pH=7 with HCl and then extracted EtOAc (500 mL.x.4). The combined organic layers were dried over Na6-chloropyridin-3-ol (5.0 g, 38.60 mmol) was dissolved in water (50 mL) and placed under an N2 atmosphere. Na2CO3 (8.2 g, 77.37 mmol) was added followed by iodine (9.8 g, 38.81 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was poured into 1 M Na25203 and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2504 and concentrated to give the product of 6-chloro-2-iodopyridin-3-ol (7.0 g, yield: 70.9percent). ‘H-NMR (CDC13, 400 MHz) 7.17 (d, J= 8.4 Hz, 1H), 7.06 (d, J 8.4 Hz, 1H). MS (M+H): 256 /258.Step 12-Synthesis of 6-chloro-2-iodopyridin-3-ol 6-chloropyridin-3-ol (5.0 g, 38.6 mmol) was dissolved in water (50 mL) and placed under an N6-chloropyridin-3-ol (5.0 g, 38.60 mmol) was dissolved in water (50 mL) andplaced under an N2 atmosphere. Na2C03 (8.2 g, 77.37 mmol) was added followed by iodine (9.8g, 38.81 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture waspoured into 1 M Na2S20 3 and extracted with EtOAc. The combined organic phases were washedwith brine, dried over Na2S04 and concentrated to give the product of 6-chloro-2-iodopyridin-3-20 ol (7.0 g, yield: 70.9percent). 1H-NMR (CDCh, 400 MHz) 8 7.17 (d, J = 8.4 Hz, 1H), 7.06 (d, J = 8.4Hz, 1H). MS (M+Ht: 256 /258.Compound 1 (5.0 g, 38.60 mmol) was dissolved in water (50 mL) and placed under an NReference Example 15 [Step a] To a mixed solution of compound 1 (1.00 g, 7.71 mmol) and sodium carbonate (1.71 g, 16.2 mmol) in tetrahydrofuran (5.00 mL) and water (5.00 mL) was added iodine (2.94 g, 16.2 mmol) in 3 portions at room temperature, and the mixture was stirred for 1.5 hr. The reaction solution was neutralized with 1 M-hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, filtered, and concentrated to give compound 2 (2.04 g). MS(ESI)m/z: 256 (M+1)+

Molecular Weight:255.44
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:254.89479
Monoisotopic Mass:254.89479
Topological Polar Surface Area:33.1
Heavy Atom Count:9
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes