Tributyltin Chloride → HCID 71143910, compound

Temperature

-78 °C

To a cold (−78° C.) mixture of 2,3-dimethyl-2H-thieno[3,2-c]pyrazole (400 mg, 2.63 mmol) and THF (15 mL) under a nitrogen atmosphere was added n-butyllithium (1.156 mL, 2.89 mmol) dropwise. The reaction mixture was stirred at −78° C. for 60 minutes. Tributylchlorostannane (0.855 mL, 3.15 mmol) was added, and the reaction mixture was stirred at −78° C. for 60 minutes and then warmed to room temperature with stirring over a period of 1 hour. The reaction mixture was quenched with brine (15 mL) and extracted with EtOAc (2×25 mL). The organic layers were combined, dried over sodium sulfate, and evaporated. The resulting residue was purified by silica gel column (80 g) chromatography, eluting with a gradient of 0-100% hexane and EtOAc. The pure product fractions were combined and evaporated to give the title compound as a gray solid (1.060 g, 2.402 mmol, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 0.78-0.99 (m, 9H), 1.06-1.22 (m, 6H), 1.23-1.46 (m, 6H), 1.48-1.70 (m, 6H), 2.46 (s, 3H), 3.96 (s, 3H), 7.03 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C19H34N2SSn, 443. found, 443.

1. stirringthe reaction mixture was stirred at −78° C. for 60 minutes
2. temperaturewarmed to room temperature
3. stirringwith stirring over a period of 1 hour
4. customThe reaction mixture was quenched with brine (15 mL)
5. extractionextracted with EtOAc (2×25 mL)
6. dry with materialdried over sodium sulfate
7. customevaporated
8. customThe resulting residue was purified by silica gel column (80 g) chromatography
9. washeluting with a gradient of 0-100% hexane and EtOAc
10. customevaporated

ORD record

ord-1c65f6ac30324f3ea4ec7e0157a406ed

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056873B2