Potassium Cyanide → 1-(4-cyano-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

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Reaction Steps

To a mixture of 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (200 mg, 1.0 eq) in H2O (4 mL) and conc. HCl (0.5 mL) was dropped the materials of NaNO2 (1.1 eq) in 1 mL of H2O at 0° C., the mixture was stirred at room temperature for 30 minutes. Then this mixture was added to another flask contained CuCN (9.0 eq), KCN (8.8 eq) and 2 mL H2O at 0° C., maintained stiffing for 5 h. At the end of reaction, FeSO4 aqueous was added to the mixture, filtrated and washed the solid substance with DMSO, evaporated the filtrate to give the crude product, which was purified by HPLC to afford 1-(4-cyano-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (20 mg, 10%). MS (ESI) 357.0 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.48 (br, 1H), 8.47 (d, J=4.5 Hz, 2H), 7.83 (d, J=4.5 Hz, 1H), 7.79 (bd, 1H), 7.72 (bs, 2H), 7.52 (d, J=4.5 Hz, 1H), 7.45 (t, J=4.5 Hz, 1H), 6.61 (m, 2H), 3.3 (overlap with DMSO-d6, 1H), 3.10-3.25 (m, 1H), 2.70-2.80 (m, 1H), 2.20-2.27 (m, 1H).

Provenance & Evidence