Reaktion #44531

ord-a766dcecfe7e4418a543639f2fa6f672

Reaktionsgleichung

COc1cc(Nc2cncc(Cl)n2)cc(OC)c1OC
2a
COc1cc(Nc2cncc(Cl)n2)cc(OC)c1OC
2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine
OB(O)c1ccccc1
phenylboronic acid
COc1cc(Nc2cncc(-c3ccccc3)n2)cc(OC)c1OC
pure title compound
Ausbeute 36.2%
COc1cc(Nc2cncc(-c3ccccc3)n2)cc(OC)c1OC
2-(3,4,5-trimethoxyphenylamino)-6-phenylpyrazine
Ausbeute 36.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07737152B2uspto-grants-2010_06