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

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Reaction Steps

1-(4-Methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-ylboronic acid (1.8 g, 5.8 mmol) was dissolved in CH2Cl2 (120 mL) and pyridine (10 mL) with molecular sieves (activated, 4 A) and the solution was kept overnight at RT. Commercially available ethyl 3-t-butyl-1H-pyrazole-5-carboxylate (1.2 g, 5.8 mmol), Cu(OAc)2 (1.1 g, 5.8 mmol) and molecular sieves (4 Å activated, powder) were added to the boronic acid solution and the reaction mixture was stirred open to the air at RT for 3 days. The reaction mixture was filtered through a pad of Celite®, and the filtrate was evaporated under reduced pressureand purified by silica gel column chromatography to yield ethyl 1-(1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylate (2.5 g, 94% yield). LC-MS (EI) m/z: 460.3 (M+H+).

Provenance & Evidence