Ethanol → Ethyl 4-amino-5-(3-fluoro-4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of EtOH (75 mL) was added ethyl 1-amino-5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (1.68 g, 5.28 mmol) and formamidine acetate (5.49 g, 52.8 mmol). The solution was heated to 80° C. for 17 h. Upon cooling to rt the solution was treated with water and a precipitate formed which was filtered and washed with additional water. The solid was then suspended in DCM and Et2O. The solid was collected and washed with Et2O yielding 1.22 g of an orange-yellow solid (3.52 mmol, yield 67%). 1H-NMR (DMSO-d6) δ 8.20 (s, 1H), 8.18 to 8.14 (t, J=8.2 Hz, 1H), 7.97 (s, 1H), 7.66 to 7.63 (d, J=12.4 Hz, 1H), 7.41 to 7.39 (d, J=8.4 Hz, 1H), 4.12 to 4.07 (q, J=7.0 Hz, 2H), 1.13 to 1.10 (t, J=7.0 Hz, 3H); MS [M+H]+=346.2; LCMS RT=2.77 min.

Provenance & Evidence