ethyl indolizine-2-carboxylate synthesis

6synthesis methods

Product Name:ethyl indolizine-2-carboxylate
CAS Number:153274-63-6
Molecular formula:C11H11NO2
Molecular Weight:189.21

2-Pyridinepropanoic acid, β-(acetyloxy)-α-methylene-, ethyl ester

153274-58-9
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153274-63-6
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Yield:153274-63-6 75%

Reaction Conditions:

at 120; for 0.916667 h;Inert atmosphere;

Steps:

7 Ethyl(indolizine-2-carboxylate) (3)

To a 25 mL flask was added ethyl 2-(acetoxy(pyridin-2- yl)methyl)acrylate (7.0 g, 28 mmol). The acrylate was set to stir at 120 °C under a nitrogen atmosphere. After 55 min, the reaction was judged complete by TLC. The reaction mixture was diluted in 50 mL 5% MeOH: EtOAc and passed through a thick pad of SiO₂ using 5% MeOH: EtOAc as eluent. Concentrated to give a dark solid (4.02 g, 21.2 mmol, 75%). ¹H NMR (300 MHz, CDCl₃) δ 7.85 (d, J= 6.3 Hz, 1.0 Hz, lH), 7.80 (s, 1H), 7.36 (d, J = 9.2 Hz, 1H), 6.83 (s, 1H), 6.68 (dd, J = 9.0 Hz, 6.3 HzlH), 6.53 (td, J= 6.9 Hz, 1,2 Hz, 1H), 4.35 (q, J= 7.1 Hz, 2H), 1.38 (t, J= 7.1 Hz, 3H).

References:

WO2016/19182,2016,A1 Location in patent:Page/Page column 33; 35