Tetrahydrofuran → HCID 57794642, compound

Participants

Reaction Steps

To a suspension of (±)-methyl 2-(1-hydroxy-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl)isonicotinate (233 mg, 0.527 mmol 1.0 equiv) and 4-nitrophenyl 4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate (251 mg, 0.632 mmol, 1.2 equiv) in tetrahydrofuran (6 mL) was added sodium hydride (91 mg, 7 equiv) in one portion. The resulting mixture was stirred at room temperature under nitrogen overnight. The mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was acidified to pH 5 with acetic acid. The aqueous portion was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash column chromatography (20% methanol in methylene chloride) to afford the desired acid (227 mg, 62.8%) as a tan solid. (ESI) 685 (MH)+. HPLC tR=2.19 min.

Provenance & Evidence