4-Toluenesulfonyl chloride → 4-bromo-5-isopropyl-1-tosyl-1H-indazole

Participants

Reaction Conditions

Reaction Steps

NaH (60% dispersion in mineral oil, 241 mg, 6.02 mmol) was added to a solution of 4-bromo-5-isopropyl-1H-indazole (720 mg, 3.01 mmol) in THF (15 mL) at 0° C. After 10 min, TsCl (861 mg, 4.52 mmol) was added and the resulting mixture was stirred at 0° C. for 1 h, then at room temperature overnight. Saturated aqueous NH4Cl was added and the mixture was extracted with EtOAc (2×). The combined organics were washed with brine, dried (Na2SO4) and concentrated. Ther residue was purified by silica gel chromatography (0-30% EtOAc/heptanes) to provide 4-bromo-5-isopropyl-1-tosyl-1H-indazole. MS (ESI+) m/z 394.8 (M+H)+.

Provenance & Evidence