Tributyltin Chloride → HCID 71143890, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) mixture of 1-methyl-1H-thieno[3,2-c]pyrazole (200 mg, 1.447 mmol) in THF (10 mL) was added n-butyllithium (0.637 mL, 1.592 mmol) dropwise under a nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 60 minutes. Tributylchlorostannane (0.471 mL, 1.737 mmol) was added, and the reaction mixture was stirred at −78° C. for 60 minutes and then warmed to room temperature over a period of 2 hours. The reaction was quenched with brine (20 mL) and extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried over sodium sulfate, concentrated, and purified via flash chromatography, eluting with 20% EtOAc and hexane to give the title compound as a clear oil (420 mg, 68%). 1H NMR (400 MHz, CDCl3) δ ppm 0.76-0.99 (m, 9H), 0.99-1.22 (m, 6H), 1.22-1.51 (m, 6H), 1.51-1.72 (m, 6H), 4.02 (s, 3H), 6.87 (d, J=0.51 Hz, 1H), 7.58 (s, 1H).

Provenance & Evidence