5-Bromo-2-methoxy-3-pyridinecarbonitrile

12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0°C are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70°C overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50°C to yield 1 1.6 g (73percent) of 5-bromo-2- methoxy-nicotinonitrile in the form of a white solid. LCMS (EI, m/z): (M+l) 214.951H MR: δΗ ppm (400 MHz, DMSO): 8.61 (1H, d, CHExample 2b 12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0°C are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70°C overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50°C to yield 11.6 g (73percent) of 5-bromo-2-methoxy-nicotinonitrile in the form of a white solid. LCMS (EI, m/z): (M+1) 214.95 Example 2b: 5-bromo-2-methoxy-nicotinonitrile 12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0°C are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70°C overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50°C to yield 11.6 g (73percent) of 5-bromo-2- methoxy-nicotinonitrile in the form of a white solid. LCMS (EI, m/z): (M+l) 214.95 1H NMR: δΗ ppm (400 MHz, DMSO): 8.61 (1H, d, CHExample 2b: 5-bromo-2-methoxy-nicotinonitrile 12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0°C are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70°C overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50°C to yield 11.6 g (73percent) of 5-bromo-2- methoxy-nicotinonitrile in the form of a white solid. LCMS (EI, m/z): (M+l) 214.95 1H NMR: δΗ ppm (400 MHz, DMSO): 8.61 (1H, d, CH12.23 g (149 mmol) of sodium acetate and then 7.66 ml (149 mmol) of bromine at 0°C are added to 10 g (74.6 mmol) of a solution of 2-methoxy-nicotinonitrile in 29 ml of acetic acid. The reaction mixture is heated at 70°C overnight. After returning to room temperature, the reaction medium is added to an ice bath and the precipitate obtained is filtered, rinsed with water and then dried at 50°C to yield 11.6 g (73percent) of 5-bromo-2-methoxy-nicotinonitrile in the form of a white solid. LCMS (EI, m/z): (M+1) 214.95 2-Methoxy-nicotinonitrile (4.0 g, 30.0 mmol) obtained in the above Step 1 was dissolved in After dissolving in acetic acid (100 mL), sodium acetate (4.92 g, 60.0 mmol), After adding bromine (3.08 mL, 60.0 mmol), the mixture was stirred at 70 DEG C for 12 hours, And cooled to room temperature.The resulting solid was separated, washed with water and dried to give 5-bromo-2-methoxy-nicotinonitrile (4.1G, 65percent yield).

Molecular Weight:213.03
XLogP3:1.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:211.95853
Monoisotopic Mass:211.95853
Topological Polar Surface Area:45.9
Heavy Atom Count:11
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes