Imidazole → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

Participants

Reaction Steps

In a round-bottomed flask, 5-hydroxy-1H-indazole (700 mg, 5.22 mmol) was dissolved in DMF (15 ml) and TBDMS-Cl (865 mg, 5.74 mmol) and imidazole (426 mg, 6.26 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 1.21 g (93%) of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indazole as an off-white solid.

Provenance & Evidence