4-Bromobutyronitrile → Ethyl 1-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

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Reaction Steps

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was reacted with NaH and 4-bromobutyronitrile in DMF under the same conditions as for example 22, step A to give a crude solid which was purified by column chromatography on silica gel (50% EtOAc/hexanes as eluant). Ethyl 1-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as a white solid (67%), m.p. (EtOAc) 157-159° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.30 (s, 1H), 8.51 (s, 1H), 7.77 (dd, J=10.1, 1.9 Hz, 1H), 7.61 (br d, J=8.4 Hz, 1H), 7.30 (t, J=8.5 Hz, 1H), 5.46 (s, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.96 (t, J=7.2 Hz, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.93 (pentet, J=7.2 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H). Anal. Calcd for C18H17FIN3O3: C, 46.1; H, 3.7; N, 9.0. Found: C, 46.4; H, 3.6; N, 8.9.

Provenance & Evidence