NSC 600157 synthesis

Yield: 69%

Reaction Conditions:

in ethanol at 20; for 2 h;

Steps:

2-(Pyridin-3-ylmethylene)-1H-indene-1,3(2H)-dione⁴ 14d
Pyridine-3-carbaldehyde (1.28 mL,1.47 g, 13.7 mmol) was added to a stirring suspension of inden-1,3-dione (2.0 g, 13.7 mmol) in ethanol(30 mL) at r.t. After 2 h the reaction mixture was cooled in an ice bath, a precipitate was filtered and recrystallized from i-PrOH. Yield 2.22 g (69%), green crystals; mp 160-161 °C. ¹H NMR (CDCl₃, 400MHz): δ = 7.46 (dd, J = 8.0, 4.8 Hz, 1H, pyr-H⁵); 7.82-7.85 (m, 2H, H^Ind); 7.85 (s, 1H, C=CH); 8.00-8.04(m, 2H, H^Ind); 8.71 (d, J = 4.8 Hz, 1H, pyr-H⁶); 9.15 (dd, J = 8.0, 1.6 Hz, 1H, pyr-H⁴); 9.18 (s, 1H, pyr-H2) ppm. ¹³C NMR (CDCl₃, 100 MHz): δ = 123.5, 123.6 (C4,7, pyr-C⁵); 129.0; 131.3 (C2, pyr-C³); 135.6,135.7 (C^5,6); 139.7 (pyr-C⁴); 140.2, 142.44 (C^3a,7a); 142.37 (C=CH); 152.9, 154.8 (pyr-C^2,6); 188.7, 189.3(C=O) ppm. HRMS (ESI), m/z: calcd for C15H9NO2 [M+H]⁺ 236.0706, found 236.0711.

References:

Pankova, Alena S.;Kuznetsov, Mikhail A. [Tetrahedron Letters,2014,vol. 55,# 15,p. 2499 - 2503] Location in patent:supporting information