Sodium hydride → HCID 23631096, compound

Participants

Reaction Steps

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was reacted with NaH and 1-bromo-2-(2-methoxyethoxy)ethane 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 4-(2-fluoro-4-iodoanilino)-1-[2-(2-methoxyethoxy)ethyl]-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as a pale yellow oil (41%). 1H NMR [(CD3)2SO, 400 MHz] δ 9.30 (s, 1H), 8.43 (s, 1H), 7.77 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (ddd, J=8.3, 1.9, 0.8 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.44 (d, J=1.3 Hz, 1H), 4.31 (q, J=7.1 Hz, 2H), 4.06 (t, J=5.1 Hz, 2H), 3.61 (t, J=5.2 Hz, 2H), 3.54-3.50 (m, 2H), 3.43-3.39 (m, 2H), 3.22 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). HRMS (EI+) calcd C19H22FIN2O5 (M+) 504.0558, found 504.0552.

Provenance & Evidence