Diethyl Ether → HCID 86594759, compound

Participants

Reaction Steps

To a cold solution (−40° C.) of 1-(2-bromo-pyridin-3-yl)-2,2-dimethyl-propan-1-ol (8.18 g, 33.5 mmol) (Romero, D. L. et al. J. Med. Chem. 1994, 37, 999-1014) in dry THF (310 mL) was added dropwise a solution of 1.6 M MeLi in Et2O (23.1 mL, 36.9 mmol). The solution was warmed to room temperature and stirred 15 min before the addition of carbon disulfide (2.22 mL, 36.9 mmol). The solution was stirred 50 min and then MeI (2.50 mL, 40.2 mmol) was added. The mixture was stirred 1.5 h and was quenched with a saturated solution of NaHCO3 (100 mL). The solution was extracted with Et2O (3×120 mL). The combined organic portions were dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (5% EtOAc/hexanes) to afford 8.58 g (81%) of Dithiocarbonic acid [1-(2-bromo-pyridin-3-yl)-2,2-dimethyl-propyl]ester methyl ester as a yellow oil. 1H NMR (CDCl3) δ 1.09 (s, 9H), 2.55 (s, 3H), 6.50 (s, 1H), 7.26 (dd, 1H, J=4.7, 7.7 Hz), 7.60 (dd, 1H, J=2.0, 7.7 Hz), 8.30 (dd, 1H, J=1.9, 4.7 Hz).

Provenance & Evidence