Sodium Carbonate → HCID 178518682, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure flask with stir bar, the intermediate from Example 10 Step A (75mg, 0.16 mmol), 2-bromo-5-chloropyridine (33.5 mg, 0.17 mmol), and (Ph3P)2PdCl2 (11.1 mg, 0.02 mmol) were added. The flask was purged of air and back-filled with argon (3×). Toluene (0.79 ml) and ethanol (0.79 ml) were bubbled with argon for at least 10 min before addition to the flask. Na2CO3 (0.24 ml, 0.48 mmol) was bubbled with argon, and then added to the flask. The mixture was heated at 90° C. in an oil bath overnight. Water was added to quench the reaction. The water layer was extracted with ethyl acetate 3×. The combined organics were washed with brine, dried with MgSO4, filtered, and concentrated in vacuo. The crude compound was purified by reverse phase HPLC (10-100% acetonitrile in H2O+0.05% TFA) to afford a light yellow solid. 1H NMR (600 MHz, CD3OD) δ 14.00 (m, 1H), 11.40 (m, 1H), 10.97 (s, 1H), 8.73 (s, 1H); 8.53 (d, 1H); 8.29 (s, 1H); 8.05 (s, 2H); 7.56 (m, 3H); 7.25 (d, 2H): [M+H]+ 459.

Provenance & Evidence