5-BROMO-3-IODO-PYRIDIN-2-OL

Will contain 5-bromo-2-hydroxypyridine (2.5 g, 14.4 mmol), A mixture of iodosuccinimide (4.7 g, 20.9 mmol) and acetonitrile (40 mL) was stirred at 82 ° C for 20 min. After cooling to room temperature, filtration, the cake was recrystallized from ethyl acetate to give 5-bromo-2-hydroxy-3-iodopyridine (65) (4.0 g). The yield was 92.6percent.To 5-bromo-2-hydroxypyridine I (5g, 29mmol) was added solid N Jodosuccinimide (7.lg, 32mmol) in acetonitrile (l2OmL). The solution was stirred at reflux for 4 hours and followed by TLC. The solution was cooled to room temperature, filteredand washed with methanol. 5-bromo-2-hydroxy-3-.iodopyridine 2 was obtained as a pink solid (yield: 83percent).Synthesis of 5-bromo-3-iodopyridin-2-ol (218): 5-Bromopyridin-2-ol (1.74 g, 10 mmol) was dissolved in DMF (40 mL) and NIS (2.7 g, 12 mmol) was added at room temperature. The reaction mixture was heated at 50 °C for 6 h. The reaction mixture was cooled down to room temperature, poured into 50 mL of water, extracted with EtOAc (60 mL X 3). The combined organic layers were washed with brine, dried over anhydrous NaTo a solution of 5-bromo-2-(1H)-pyridone (18.8 gWill contain 5-bromo-2-hydroxypyridine (2.5 g, 14.4 mmol), A mixture of iodosuccinimide (4.7 g, 20.9 mmol) and acetonitrile (40 mL) was stirred at 82 C for 20 min. After cooling to room temperature, filtration, the cake was recrystallized from ethyl acetate to give To 5-bromo-2-hydroxypyridine I (5g, 29mmol) was added solid N Jodosuccinimide (7.lg, 32mmol) in acetonitrile (l2OmL). The solution was stirred at reflux for 4 hours and followed by TLC. The solution was cooled to room temperature, filteredand washed with methanol. 5-bromo-2-hydroxy-3-.iodopyridine 2 was obtained as a pink solid (yield: 83%).Synthesis of To a solution of To contain Compound 65 (4.0 g, 13.3 mmol), Cuprous iodide (254 mg, 1.33 mmol), Bis(triphenylphosphine)palladium dichloride (468 mg, 0.667 mmol) 1-pentyne (1.09 g, 16.0 mmol) was added to a mixture of triethylamine (50 mL). The resulting mixture was stirred at 50 C overnight. The solvent was evaporated under reduced pressure. water (EtOAc) The combined organic layers were washed with brine (30 mL) The solvent was distilled off under reduced pressure. The product is purified by column chromatography (200-300 mesh silica gel, ethyl acetate: petroleum ether = 1:200 to 1:100). 5-Bromo-2-propylfuro[2, 3-b]pyridine (66) (1.72 g) was obtained. The yield was 53.9%.Step 1, Method 18: 2-{5-Bromofuro[2, 3-Z>]pyridin-2-yl}benzonitrile[0215] A mixture of

Molecular Weight:299.89
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:298.84427
Monoisotopic Mass:298.84427
Topological Polar Surface Area:29.1
Heavy Atom Count:9
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes