Reaktionsgleichung
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=1.Br[C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2.C1C=CC(P([C:38]2[C:47]([C:48]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=[C:46]3[C:41]([CH:42]=CC=C3)=[CH:40][CH:39]=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:42][C:41]1[CH:40]=[CH:39][CH:38]=[C:47]([CH3:48])[C:46]=1[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH:10][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[N:23]=[CH:22][CH:21]=[CH:20]4)[N:8]=[N:9][C:4]=2[CH:3]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
About 100 mg (0.4 mmol) of 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine and about 158 mg (0.8 mmol) of 8-bromo-quinoline were dissolved in about 10 ml toluene. About 17 mg (0.018 mmol) of Pd(dba)3, about 17 mg (0.027 mmol) of BINAP, and about 50 mg (0.226 mmol) of KOt-Bu were added to the solution. The mixture was kept at about 100° C. for about 24 hours under argon. The crude product was purified by preparative HPLC. About 50 mg [7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-quinolin-8-yl-amine (product having formula (XII)) was isolated. Yield: about 33.8%; ESI-MS: [M+H]+, 392; 1H NMR (DMSO-d6): δ 2.07 (s, 6 H), 2.79(s, 3 H), 7.19 (d, J=7.4 Hz, 2 H), 7.25 (m, 1 H), 7.71-7.79 (m, 4 H), 8.04 (s, 1 H), 8.50 (d, J=8.3 Hz, 1 H), 9.05 (m, 2 H).
Aufarbeitung
- customThe crude product was purified by preparative HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-d77cab4d96024eae81a677e37116ee5a
- Quelldatensatz
- uspto-grants-2008_11
- Patentnummer
- US07456176B2
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