1-(2-Hydroxyethyl)-1H-pyrazole → 5-(1,3-Dioxolan-2-yl)-3-[2-(1H-pyrazol-1-yl)ethoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from 300 mg (0.672 mmol) 5-(1,3-dioxolan-2-yl)-3-iodo-1-([2-(trimethylsilyl)ethoxy]methyl)-1H-indazole (Example 6A) in analogy to the procedure described in Example 21A. The procedure was modified by using 5 equivalents of 2-(1H-pyrazol-1-yl)-ethanol as the alcohol reactant and by switching to toluene as solvent. The reaction mixture was heated to 140° C. for 2 h using microwave irradiation, after which time the same amounts of catalyst and ligand were added again. This cycle was repeated one more time. The crude product thus obtained was purified by preparative RP-HPLC (acetonitrile/water gradient) to afford 153 mg (52% of th.) of the title compound.

Provenance & Evidence