4-Chlorophenylboronic acid → 2-(3,4,5-Trimethoxyphenylamino)-6-(4-chlorophenyl)pyrazine

HRID 16251

Reaktionsgleichung

Reaktionsgleichung von HRID 16251
[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].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=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:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[N:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Komponenten

3

Edukt 2

HCID 742994-Chlorophenylboronic acidHCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Produkt 1

HCID 115162502-(3,4,5-Trimethoxyphenylamino)-6-(4-chlorophenyl)pyrazineAusbeute 71 %

Versuchsvorschrift

Using Method B with 212 mg (0.72 mmol) 2a and 135 mg (0.86 mmol) 4-chloro-phenylboronic acid, 190 mg pure title compound (59.7%) were obtained after purification by preparative HPLC (eluent:AcOEt). Reaction time: 18 hours. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.63 (s, 3H, CH3O(4′)), 3.82 (s, 6H, CH3O(3′+5′)), 6.88 (d, 2H, Harom(2′+6′), J=8.52), 7.24 (s, 2H, Harom(2+6)), 7.97 (d, 1H, Harom (3′+5′)), 8.05 (s, 1H, HP5), 8.40 (s, 1H, HP3), 9.46 (s, 1H, OH), 9.82 (s, 1H, NHamine); MS, (C19H18ClN3O4), m/z: 354.3 [M++1, 100].

Quellen und Nachweise

ORD-Eintrag
ord-d48bf47a077543449d285520d983b2be
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

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