ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate → ethyl 3-t-butyl-1-(2-oxo-1,2-dihydroquinolin-6-yl)-1H-pyrazole-5-carboxylate

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Reaction Steps

A solution of ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1 H-pyrazole-5-carboxylate (1.5 g, 3.3 mmol) in TFA (25 mL) was heated in a sealed tube at 100° C. for 7 h. The mixture was cooled, concentrated and purified by silica gel column chromatography to yield ethyl 3-t-butyl-1-(2-oxo-1,2-dihydroquinolin-6-yl)-1H-pyrazole-5-carboxylate (1.0 g, 90% yield). 1H NMR (400 MHz, CDCl3): δ 7.95 (d, J=9.6 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.66 (dd, J=2.4, and 8.4 Hz, 1H), 7.46 (d, J=8.8 Hz, 1H), 6.94 (s, 1H), 6.82 (d, J=9.2 Hz, 1H). LC-MS (EI) m/z: 340.3 (M+H+).

Provenance & Evidence