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

Participants

Reaction Steps

To a solution of 3-iodo-1-methyl-6-(trifluoromethyl)-1H-indazole (491 mg, 1.51 mmol) in dry tetrahydrofuran (20 mL) was added drop-wise isopropylmagnesium chloride (1.66 mL, 2M in THF, 3.31 mmol) at −16° C. under N2 atmosphere. After stirring for 20 minutes, tributylchlorostannane (0.49 mL, 1.81 mmol) was added drop-wise at −16° C., then it was warmed to room temperature for 2 h. NH4Cl solution (2 mL) was added and product was extracted with dichloromethane (150 mL), then washed with water (3×20 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to afford 1-methyl-3-(tributylstannyl)-6-(trifluoromethyl)-1H-indazole (0.98 g, crude) as yellow oil which was used to next step without further purification. 1H NMR (300 MHz, CDCl3): δ 7.79 (d, 1H, J=11.4 Hz), 7.70 (s, 1H), 7.32 (d, 1H, J=8.4 Hz), 1.48-1.32 (m, 6H), 1.25-1.18 (m, 12H), 0.92-0.79 (m, 9H).

Provenance & Evidence