Tributyltin Chloride → 6-chloro-3-(tributylstannyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-chloro-3-iodo-1H-indazole (1.11 g, 4.0 mmol) in THF (25 mL) was added sodium hydride (192 mg, 4.8 mmol). After 15 min the mixture was cooled to −16° C. Isopropylmagnesium chloride (3.00 mL, 6.00 mmol) was added dropwise and the mixture stirred at −16° C. for 2 h. Tributyltin chloride (1.56 g, 1.3 mL, 4.8 mmol) was then added and the reaction mixture warmed to room temperature. After 15 h the mixture was diluted with water and ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) filtered and concentrated in vacuo. The crude brown oil was used directly in the next step without further purification.

Provenance & Evidence