[O:1]=[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[F:10][C:11]([F:23])([F:22])[O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Cu+2].CS(C)=O>[O:1]=[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:16]1[CH:15]=[CH:14][C:13]([O:12][C:11]([F:10])([F:22])[F:23])=[CH:18][CH:17]=1In a microwave vial were placed 2-oxo-1,2-dihydropyridine-3-carbaldehyde 1-1 (200 mg, 1.62 mmol), 4-trifluoromethoxyphenylboronic acid 4-1 (660 mg, 3.25 mmol), and anhydrous Cu(OAc)2 (295 mg, 1.62 mmol). To the mixture was added DMSO (3.20 mL) followed by Et3N (0.45 mL, 3.25 mmol). The mixture was irradiated in microwave apparatus (Biotage) at 100° C. for 15 minutes and cooled to room temperature. The mixture was concentrated and the residue was purified by silica gel chromatography (0-20% EtOAc in hexane) to give 105 mg (25%) of 2-2 as a pale yellow solid: 1H NMR (300 MHz, CDCl3) δ 10.34 (1H, s), 8.13 (1H, dd, J=6.9, 2.1 Hz), 7.63 (1H, dd, J=6.9, 2.1 Hz), 7.47-7.36 (4H, m), 6.44 (1H, t, J=6.9 Hz); ESI-MS m/z 284 [C13H8F3NO3+H]+.
Loading…
