Tributyltin Chloride → 1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole

Participants

Reaction Steps

To a solution of 3-iodo-1-methyl-5-(trifluoromethyl)-1H-indazole (400 mg, 1.2 mmol) in dry THF (15 mL) was added isopropylmagnesium chloride (0.7 mL, 1.3 mmol, 2 M in THF) drop-wise at −16° C. under nitrogen atmosphere, stirred for 30 minutes, then tributylchlorostannane (0.4 mL, 1.3 mmol) was added drop-wise at −16° C. under nitrogen, the reaction mixture was warmed to room temperature slowly and stirred for 2 hours, then quenched with a solution of saturated NH4Cl (40 mL) and product extracted with EtOAc (3×30 mL) then dried over Na2SO4, filtered and concentrated, under reduced pressure to give 1-methyl-3-(tributylstannyl)-5-(trifluoromethyl)-1H-indazole (500 mg, crude) as an oil which was used directly to next step without any further purification.

Provenance & Evidence