Toluene → 6-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (0.80 g, 2.44 mmol), cyclopropylboronic acid (377 mg, 4.39 mmol), palladium(II) acetate (28 mg, 0.125 mmol), potassium phosphate tribasic (1.04 g, 4.88 mmol), toluene (9 ml) and water (0.9 ml). The reaction mixture was stirred at 100° C. in an oil bath overnight then cooled to room temperature, quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-5% EtOAc) to afford 670 mg (90%) of 6-cyclopropyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole as a light yellow oil.

Provenance & Evidence