3-Pyridinecarbonitrile, 5-bromo-1,2-dihydro-6-(1-methylethyl)-2-oxo- synthesis

3synthesis methods

Product Name:3-Pyridinecarbonitrile, 5-bromo-1,2-dihydro-6-(1-methylethyl)-2-oxo-
CAS Number:1416146-12-7
Molecular formula:C9H9BrN2O
Molecular Weight:241.08

3-Pyridinecarbonitrile,1,2-dihydro-6-(1-methylethyl)-2-oxo-(9CI)

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3-Pyridinecarbonitrile, 5-bromo-1,2-dihydro-6-(1-methylethyl)-2-oxo-

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Yield:-

Reaction Conditions:

with N-Bromosuccinimide in 1,2-dichloro-ethane at 20; for 3 h;Reflux;

Steps:

1.C

Step C: 5-bromo-6-isopropyl-2-oxo-l,2-dihydropyridine-3-carbonitrile (4). To a solution of 2- hydroxy-6-isopropylnicotinonitrile (3; 3.0 g, 19 mmol) in 50 mL of DCE was added NBS (5 g, 28 mmol) at room temperature. The reaction mixture was then heated at reflux for 3 hours. After LC-MS showed the completion of reaction, the mixture was cooled to room temperature and poured into water and extracted with methylene chloride. The combined organic layer was dried over anhy. Na₂S0₄ and concentrated in vacuo. Column chromatography (4% MeOH/DCM) afforded 3.9 g of title compound as a brown solid. MS (ES) M+H expected 241.0, found 240.9. 1H NMR (DMSO-d₆) δ 12.58 (br. s., 1H), 8.38 (s, 1H), 3.25 - 3.32 (m, 1H), 1.23 (s, 3H), 1.21 (s, 3H).

References:

WO2012/171337,2012,A1 Location in patent:Page/Page column 111

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