Tributyltin Chloride → 1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 3-iodo-1-methyl-4,5,6,7-tetrahydro-1H-indazole (62 mg, 237 μmol) was dissolved in THF (3 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride 2 M in THF (132 μL, 265 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min. Then, tributylchlorostannane (88.6 mg, 73.8 μL, 272 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 (3×30 mL), organics dried over MgSO4 and concentrated to an off-white waxy solid. The residue was dried under high vacuum yielding 1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole assumed quantitative and taken into next step without further treatment.

Provenance & Evidence