Triethylamine → HCID 59686869, compound

Participants

Reaction Steps

To a stirred solution of 2-methoxycarbonylpyridine-4-methanol (222 mg, 1.3 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (279 μl, 2 mmol) and methanesulfonyl chloride (120 μl, 1.5 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with (73) (394 mg, 1.3 mmol), powdered anhydrous potassium carbonate (183 mg, 1.3 mmol), and lithium iodide (178 mg, 1.3 mmol). DMF (7 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (4:1)) to afford 271 mg (45%) of a white foam. 1H-NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=6.8 Hz), 1.23 (3H, d, J=6.8 Hz), 2.23 (1H, m), 2.37 (3H, s), 4.00 (3H, s), 4.66 (1H, d, J=17.0 Hz), 5.11 (1H, d, J=17.0 Hz), 7.23 (1H, m), 7.65 (2H, s), 7.73 (1H, s), 7.88 (1H, s), 8.55 (1H, d, J=5.2 Hz), 9.56 (1H, s).

Provenance & Evidence