3-Pyridine aldoxime → HCID 11993992, compound

Participants

Reaction Steps

To a solution of 33 (161 mg, 1.3 mmol) in anhydrous DMF (5 mL) at 0° C. was added N-chlorosuccinimide (202 mg, 1.3 mmol) portionwise over 20 min. The resultant solution was heated to 50° C. and stirred for 50 min. The solution was cooled to room temperature and transferred to a flask containing CH2Cl2 (3 mL). To the solution was added a solution of tert-butyl prop-2-ynylcarbamate (204 mg, 1.3 mmol) in CH2Cl2 (3 mL), the solution was cooled to 0° C. and triethylamine (0.18 mL, 1.3 mmol) was added dropwise, the ice bath was removed and the solution was stirred at ambient temperature for 3 h. To the solution was added saturated aqueous sodium bicarbonate (30 mL), the organic fraction was collected and the aqueous fraction was extracted with CH2Cl2 (2×15 mL), back washed with water (30 mL), and brine (30 mL), dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 50/50, Rf=0.16) to afford the title compound 34 (212 mg, 59% yield) as a an off white solid: mp=67-69° C.; 1H NMR (CDCl3) δ 8.93 (br s, 1H), 8.62 (m, 1H), 8.05 (m, 1H), 7.34 (m, 1H), 6.50 (s, 1H); 5.63 (br s, 1H); 4.43 (d, J=6 Hz, 1H), 1.40 (s, 9H); LRMS (ESI) calcd for C14H18N3O3 [M+H]+ 276. found 276.

Provenance & Evidence