Sodium Hydroxide → 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylic acid

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Reaction Steps

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylate was dissolved in EtOH and treated with 1 M NaOH, as for example 1, step C, to hydrolyse the ester to give 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylic acid as a pale yellow solid (88%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.33 (v br s, 1H), 9.67 (br s, 1H), 8.46 (s, 1H), 7.77 (dd, J=10.0, 1.8 Hz, 1H), 7.60 (dd, J=8.3, 0.9 Hz, 1H), 7.32 (t, J=8.5 Hz, 1H), 5.50 (s, 1H), 4.60-4.56 (m, 1H), 4.12-4.06 (m, 2H), 3.79-3.71 (m, 1H), 3.60-3.35 (m, 3H), 1.75-1.27 (m, 6H). LCMS (APCI−) calcd for C19H19FIN2O5 501 (MH+), found 501.

Provenance & Evidence