Tributyltin Chloride → 3-(5-(difluoromethoxy)-3-(tributylstannyl)-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine

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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, stirred for 30 minutes, tributylchlorostannane (3.3 mL, 3.6 mmol) was added drop-wise at −16° C. under nitrogen, then the reaction mixture was warmed to room temperature slowly and stirred for 2 hours. Then the reaction mixture was quenched with a saturated solution of NH4Cl (40 mL) and extracted with EtOAc (3×30 mL), the combined organic layer were dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-(5-(difluoromethoxy)-3-(tributylstannyl)-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine, (1.1 g, 71%) as an oil, used into the next step without purification.

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