Sodium hydride → tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

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Reaction Steps

Compound 353 (270 mg, 0.87 mmol), 2-nitro-5-(thiophen-2-yl)benzenamine (3, 193 mg, 0.87 mmol), and BOP (386 mg, 0.87 mmol) were dissolved in dry pyridine (10 mL). Sodium hydride (140 mg, 3.50 mmol) was added and the resulting solution was stirred at room temperature for 2 hours, quenched with glacial acetic acid (1 mL), and the pyridine was removed under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The extract was dried with sodium sulphate and evaporated to yield a residue which was triturated with ethyl acetate for 15 minutes, to afford the title compound 354 as a yellow solid (270 mg, 61% yield). 1H NMR: (DMSO) δ 10.79 (s, 1H), 8.06-8.04 (m, 2H), 7.86 (d, J=3.9 Hz, 1H), 7.75-7.68 (m, 3H), 7.25-7.20 (m, 2H), 6.32 (s, 1H), 4.04-4.01 (m, 2H), 3.54 (t, J=5.3 Hz, 2H), 1.43 (s, 9H).

Provenance & Evidence