5-BROMO-3-CYANO-2-HYDROXYPYRIDINE

5-Bromo-2-oxo-1, 2-dihydropyridine-3-carbonitrile(12) To a stirring solutionof compound 11 (50 mg, 0.42 mmol)and NaOAc (69 mg, 0.84 mmol) in 5 mL glacial AcOH at room temperature was addedBr5-Bromo-2-chloronicotinonitrile (13) Compound 12 (69 mg, 0.35 mmol) and PCl5(109 mg, 0.52 mmol) were refluxed in POCl3 (5 mL) overnight. Themixture was cooled to room temperature and added to ice water in drops slowly, basified with NaOH (4 M)to pH 8, and extracted with CH2Cl2 (3×30 mL). Thecombined extracts were washed with aqueous NaHCO3, brine, dried overanhydrous Na2SO4, and concentrated in vacuum.Purification by chromatography (PE/EA = 20:1) provided compound 13 (63 mg, 84percent) as a yellow solid. MP:138~139°C. 1H NMR (400 MHz, CDCl3): delta 8.66 (d, J = 2.4 Hz, 1H), 8.12 (d, J = 2.4 Hz, 1H).65-Bromo-2-chloro-nicotinonitrile 5-Bromo-2-oxo-1, 2 dihydro-pyridine-3-carbonitrile (33 g, 166 mmol) was added to a suspension of PCl5 (96.6 g, 464 mmol) in POCl3 (20 ml, 216 mmol). The mixture was stirred at reflux for 3 hours, cooled to room temperature and then poured slowly into ice/water. The resulting solid was fitered, washed with water, and dried in vacuo to afford the title compounid. 1H NMR delta (d6 DMSO) 8.7 (d, 1H), 8.1 (d, 1H).Acetic acid (34 ml) was added to 2-oxo-1, 2-dihydropyridine-3-carbonitrile (6.28 g, 0.052 mol) and the mixture was heated to 130C. When the solid was dissolved, bromine (12.5 g, 0.078 mol) was added slowly and stirred at the same temperature for 3 hours.After the reaction solution was cooled to room temperature, dichloromethane and water were added. The organic layer was separated and the aqueous layer was washed with dichloromethane. The organic layer was collected, washed with brine, dried over anhydrous sodium sulfate and concentrated to give the desired compound (9.11 g, 88% yield) as a yellow solid.5-Bromo-2-oxo-1, 2-dihydropyridine-3-carbonitrile(12) To a stirring solutionof compound 11 (50 mg, 0.42 mmol)and NaOAc (69 mg, 0.84 mmol) in 5 mL glacial AcOH at room temperature was addedBr2 (21.5 muL, 0.42 mmol) for 2 h. The mixture was concentrated invacuum to remove AcOH. Purification by chromatography (EA) provided compound 12 (69 mg, 75%) as a yellow solid. MP:216~217C. 1H NMR (400 MHz, CD3COCD3): delta 11.70 (s, 1H), 8.22 (d, J= 2.8 Hz, 1H), 8.05 (d, J = 2.8 Hz, 1H).5 Brornine (29 ml, 560 mmol) was added to a stirred solution of 2-oxo-1, 2-dihydro-pyridine-3-carbonitrile (34 g, 280 mmol) in acetic acid (180 ml) at room temperature. After 14 hours the reaction mixture was concentrated in vacuo and the resulting oil was trituated with ethanol to afford the title compound as a solid. 1H NMR delta (d6 DMSO) 12.8 (brs, 1H), 8.4 (d, 1H), 8.1 (d, 1H).A mixture of 1-(1-benzyl-5-methyl-1H-pyrazol-4-yl)-2-bromoethan- 1-one (0.3 g),

Molecular Weight:199.00
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:197.94288
Monoisotopic Mass:197.94288
Topological Polar Surface Area:52.9
Heavy Atom Count:10
Complexity:281
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes