Dibutylchloro(propyl)stannane → 5-(difluoromethoxy)-3-(tributylstannyl)-1H-indazole

Participants

Reaction Steps

To a solution of 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.2 g, 2.78 mmol) in dry THF (25 mL) was added isopropylmagnesium chloride (1.5 mL, 2M in THF, 3 mmol) drop-wise at −16° C. under nitrogen atmosphere. The reaction was stirred for 30 minutes, then dibutylchloro (propyl)stannane (3.3 mL, 3.6 mmol) was added dropwise at −16° C. under nitrogen, then the reaction mixture was slowly warmed to room temperature and stirred for 2 hours. The reaction mixture was quenched with a solution of saturated NH4Cl (40 mL) and product extracted with EtOAc (3×30 mL), organics combined dried with sodium sulfate, filtered and concentrated. Crude oil used into the next step without further purification (1.1 g, crude).

Provenance & Evidence