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

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To a solution of 5-(difluoromethoxy)-3-iodo-1-methyl-1H-indazole (400 mg, 1.23 mmol) in dry THF (15 mL) was added isopropylmagnesium chloride (0.75 mL, 1.3 mmol, 2M in THF) drop-wise at −16° C. under nitrogen atmosphere, stirred for 30 minutes, then dibutylchloro(propyl)stannane (0.5 mL, 1.45 mmol) was added drop-wise, the reaction mixture was warmed to room temperature slowly and stirred for 2 hours. The reaction mixture was quenched with a saturated solution of NH4Cl (40 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure and the residue was used into the next step without purification (500 mg, crude) as oil.

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