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

Participants

Reaction Conditions

Reaction Steps

5-(3-Chlorophenoxy)-3-iodo-1-methyl-1H-indazole (0.154 g, 400 μmol) was dissolved in THF (3.00 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath) then isopropylmagnesium chloride (2M in THF, 224 μL, 448 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min then tributylchlorostannane (150 mg, 125 μL, 460 μmol) was added slowly. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction mixture was quenched with saturated ammonium chloride solution, extracted with dichloromethane, and the combined organics dried over MgSO4 and concentrated to a yellow oil. The residue was dried under high vacuum to give 5-(3-chlorophenoxy)-1-methyl-3-(tributylstannyl)-1H-indazole. The mass of this material was greater than the theoretical yield of the desired product. The yield was assumed to be quantitative, and the material was used directly in the next step without further purification.

Provenance & Evidence