Stannous Chloride → 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(4-nitro-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3.5 g, 1.0 eq) in EtOH (125 mL) was added SnCl2*2H2O (5.0 eq) in portions, the mixture was stirred at 70° C. overnight. At the end of reaction, the mixture was concentrated and ethyl acetate was added. The organic layer was washed with NaHCO3 aqueous for three times. The combined organic layer was washed with brine and dried over MgSO4, filtered and evaporated to give the crude product, which was purified by HPLC to afford 1-(4-amino-2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (3 g, 93%). MS (ESI) 347.0 (M+H); 1H NMR (300 MHz, DMSO-d6) δ12.44 (s, 1H), 8.49 (d, J=3.0 Hz, 2H), 8.46 (d, J=4.2 Hz, 1H), 7.72 (d, J=3.0 Hz, 2H), 7.57 (d, J=4.2 Hz, 1H), 6.96 (t, J=4.5 Hz, 1H), 6.57-6.61 (m, 2H), 6.45 (t, J=4.2 Hz, 1H), 6.31 (d, J=4.2 Hz, 1H), 5.19 (s, 2H), 2.85-2.90 (m, 1H), 2.65-2.75 (m, 2H), 2.00-2.05 (m, 1H).

Provenance & Evidence