Sodium hydride → HCID 67293404, compound

Participants

Reaction Conditions

Reaction Steps

To a flask was added NaH (60% in mineral oil, 0.473 g, 11.8 mmol) and THF (59.1 mL). The mixture was cooled to about 0° C. 6-Nitro-1H-indazole-3-carbaldehyde (2.26 g, 11.8 mmol, ChemPacific) was added in several smaller portions and the mixture was stirred at about 0° C. for about 20 min. SEMCl (2.30 mL, 13.0 mmol) was added dropwise and the mixture was stirred at about 0° C. for about 10 min and then stirred at rt for about 72 h. To the mixture was added saturated aqueous NH4Cl (25 mL) and water (10 mL). The aqueous layer was separated and extracted with DCM (2×50 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (80 g silica gel) eluting with 10 to 25% EtOAc/heptane to give 3-methyl-6-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (1.915 g, 50%): 1H NMR (400 MHz, DMSO) δ 10.24 (s, 1H), 8.94 (d, J=1.5 Hz, 1H), 8.36 (dd, J=6.5, 2.3 Hz, 1H), 8.31-8.13 (m, 1H), 6.08 (s, 2H), 3.58 (s, 2H), 0.83 (s, 2H), −0.12 (s, 9H).

Provenance & Evidence