Potassium Carbonate → HCID 71143769, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1H-1,2,3-triazole (410 mg, 5.93 mmol) were added copper (Cu) powder (93 mg, 1.45 mmol), K2CO3 (160 mg, 1.15 mmol) and 1 (300 mg, 0.694 mmol) under N2 atmosphere. The reaction mixture was gradually heated to 140° C. and stirred for 4 h. The reaction mixture was cooled to 100° C., quenched with ethylenediaminetetraacetic acid (EDTA) sodiuim (Na) salt solution, and made basic with sodium carbonate (Na2CO3) solution. The aqueous layer was extracted with CH2Cl2 (3×50 mL); the combined organic phases were washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (eluting with 45% EtOAc/hexane) to afford 9 (0.12 g, 0.297 mmol, 42%) as a solid. 1H NMR (500 MHz, CDCl3): δ 9.33 (s, 1H), 8.77 (s, 1H), 8.47 (dd, J=8.5, 2.0 Hz, 1H), 7.90 (s, 2H), 7.70 (d, J=9.0 Hz, 1H), 7.34-7.29 (m, 1H), 6.78-6.73 (m, 1H), 6.67-6.64 (m, 1H), 5.64 (d, J=14.0 Hz, 1H), 5.14 (d, J=14.0 Hz, 1H). MS (ESI): m/z 420.9 [M++1]. HPLC: 99.9%.

Provenance & Evidence