Dimethylformamide → Ethyl 2-(2-biphenylylmethyl)-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate

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Reaction Steps

Ethyl 2-(2-biphenylylmethyl)-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. To a solution of ethyl 5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (example 46(a), 125 mg, 0.55 mmol) in N,N-Dimethylformamide (DMF) (5 ml) at 0° C. was added sodium hydride (55 mg, 0.138 mmol) in portions. The reaction mixture was stirred at room temperature for 45 minutes and then cooled back to 0° C. and 2-phenylbenzyl bromide (101 μl, 0.55 mmol) was added. The mixture was stirred at ambient temperature for 3 hours then quenched with 1N HCl (3 ml) extracted with ethyl acetate (2×20 ml). The organic layers were combined, dried over Magnesium sulfate, filtered and solvents removed with rotary evaporation. The crude oil was purified by flash column chromatography (10-100% ethyl acetate in hexanes) to provide the title compound ethyl 2-(2-biphenylylmethyl)-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (126 mg, 0.32 mmol, 58% yield) as a pale yellow oil that was used immediately in the next step. MS (ES+) m/e 393 [M+H]+.

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