Sodium hydride → Ethyl 1-(2-tert-butoxy-2-oxoethyl)-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 t-butylbromoacetate 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 (1% MeOH/CH2Cl2 as eluant). Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as a white solid (72%), m.p. (EtOAc/hexanes) 149-151° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.34 (s, 1H), 8.57 (s, 1H), 7.78 (dd, J=10.0, 1.9 Hz, 1H), 7.61 (dd, J=8.4, 1.0 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.43 (d, J=1.2 Hz, 1H), 4.62 (s, 2H), 4.31 (q, J=7.1 Hz, 2H), 1.42 (s, 9H), 1.33 (t, J=7.1 Hz, 3H). Anal Calcd for C20H22FIN2O5: C, 46.5; H, 4.3; N, 5.4. Found: C, 46.7; H, 4.2; N, 5.5.

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