Tributyltin Chloride → HCID 71143876, compound

Temperature

-78 °C

To a cold (−78° C.) mixture of 1,3-dimethyl-1H-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 normal-phase 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 clear oil (1.060 g, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 0.77-0.98 (m, 9H), 1.04-1.20 (m, 6H), 1.25-1.47 (m, 6H), 1.49-1.70 (m, 6H), 2.41 (s, 3H), 3.94 (s, 3H), 6.82 (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 normal-phase silica gel column (80 g) chromatography
9. washeluting with a gradient of 0-100% hexane and EtOAc
10. customevaporated

ORD record

ord-1fedd0918f0a45adbdab29ba7e1e02f3

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056873B2