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122262-38-8

2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)-one synthesis

8synthesis methods
2-Buten-1-one, 1-(2-methoxy-3-pyridinyl)-3-methyl-

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Yield: 52%

Reaction Conditions:

with chloro-trimethyl-silane;sodium iodide in acetonitrile for 16 h;

Steps:

47.d
d) 2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)-one Trimethylsilyl chloride and sodium iodide were added to a stirred solution of 1-(2-methoxypyridin-3-yl)-3-methylbut-2-en-1-one (Preparation 47c, 1.30 g, 6.80 mmol) in acetonitrile (25 mL). After 16 hours, water was added and the mixture was extracted with dichloromethane. The organic extract was dried (MgSO4) concentrated and the residue was purified by flash chromatography (98:2 dichloromethane/methanol) to give the title compound (0.62 g, 52%) as a yellow solid. LRMS (m/z): 178 (M+1)+.1H NMR (300 MHz, DMSO-d6) δ ppm 1.41 (s, 6H), 2.86 (s, 2H), 7.14 (m, 1H), 8.13 (dd, 1H), 8.46 (dd, 1H).

References:

Almirall, S.A. EP2397482, 2011, A1 Location in patent:Page/Page column 65