Tributyltin Chloride → 4-(tert-Butyl)-2-(tributylstannyl)pyridine

Temperature

-76 °C

In a round-bottomed flask, 2-bromo-4-tert-butylpyridine (149 mg, 0.70 mmol) was dissolved in THF (4 mL). The colorless solution was cooled to −76° C. and n-butyllithium (1.6M solution in hexanes, 0.57 mL, 0.91 mmol) was added dropwise. The brown solution was stirred at −76° C. for 30 min then tributylchlorostannane (0.23 mL, 0.85 mmol) was slowly added. The reaction mixture was stirred at −76° C. for 15 min and then warmed to room temperature and stirred for 1.5 h. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with 50 mL EtOAc (2×). The combined organic layers were washed with 5 mL water and 5 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over 24 g SiO2 with EtOAc/Hexanes (gradient: 0-20% EtOAc). All fractions containing product were combined and concentrated to give 147 mg (30%, purity=60%) of 4-tert-butyl-2-(tributylstannyl)pyridine as a colorless oil.

1. stirringThe reaction mixture was stirred at −76° C. for 15 min
2. temperaturewarmed to room temperature
3. stirringstirred for 1.5 h
4. customThe reaction mixture was quenched with saturated aqueous NH4Cl
5. extractionextracted with 50 mL EtOAc (2×)
6. washThe combined organic layers were washed with 5 mL water and 5 mL brine
7. dry with materialthen dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was chromatographed over 24 g SiO2 with EtOAc/Hexanes (gradient: 0-20% EtOAc)
11. additionAll fractions containing product
12. concentrationconcentrated

ORD record

ord-564fb59069c84de29b5a39b44130fdbf

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2