Phenylboronic Acid → 2-(3,4,5-Trimethoxyphenylamino)-6-phenylpyrazine
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[CH:19]=[N:18][CH:17]=[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]Komponenten
3
Versuchsvorschrift
Using Method C with 200 mg (0.68 mmol) 2a and 100 mg (0.82 mmol) phenylboronic acid, 83 mg (22.9%) pure title compound were obtained after preparative HPLC (eluent: AcOEt) purification of the whole batch. Reaction time: 20 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.64 (s, 3H, CH3O(4′)), 3.83 (s, 6H, CH3O(3′+5′)), 7.26 (s, 2H, Harom(2+6)), 7.51 (m, 3H, Harom 3′+4′+5′), 8.14 (m, 2H, Harom2′+6′), 8.16 (s, 1H, HP5), 8.52 (s, 1H, HP3), 9.58 (s, 1H, NHamine); MS, (C19H19N3O3), m/z: 338 [M++1, 100].
Quellen und Nachweise
- ORD-Eintrag
- ord-a766dcecfe7e4418a543639f2fa6f672