Tributyltin Chloride → 1,6,6-trimethyl-3-tributylstannanyl-4,5,6,7-tetrahydro-1H-indazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodo-1,6,6-trimethyl-4,5,6,7-tetrahydro-1H-indazole (0.150 g, 0.49 mmol) in THF (3 mL) at 0° C. was slowly added isopropylmagnesium chloride (2.0 M in THF) (0.30 mL, 0.59 mmol). The reaction mixture was stirred at 0° C. for 20 min then tributylchlorostannane (0.16 mL, 0.59 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min then warmed to room temperature and stirred for 1 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 0% to 10% EtOAc/hexanes (0.5% Et3N) to afford 116 mg (52%) of 1,6,6-trimethyl-3-tributylstannanyl-4,5,6,7-tetrahydro-1H-indazole as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.74 (s, 3H), 2.49 (t, J=6.4 Hz, 2H), 2.30 (s, 2H), 1.45-1.61 (m, 8H), 1.25-1.41 (m, 6H), 1.04-1.13 (m, 6H), 1.01 (s, 6H), 0.89 (t, J=7.2 Hz, 9H).

Provenance & Evidence