Tetrahydrofuran → HCID 67293404, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with NaH (60% dispersion in mineral oil, 0.325 g, 13.6 mmol) and THF (40 mL). The mixture was cooled to about 0° C. followed by the addition of 3-methyl-6-nitro-1H-indazole (2.00 g, 11.3 mmol, ArkPharm). The mixture was stirred for about 30 min followed by the addition of SEMCl (2.26 g, 13.6 mmol). The mixture was warmed to rt and stirred for about 12 h. Water (5 mL) and EtOAc (70 mL) were added and the layers were separated. The organic layer was concentrated under reduced pressure to give 3-methyl-6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (3.2 g, 91%): LC/MS (Table 2, Method f) Rt=2.18 min; MS m/z: 308 (M+H)+.

Provenance & Evidence