Binap, (A+-)- → HCID 11603841, Verbindung

HRID 273497

Reaktionsgleichung

Reaktionsgleichung von HRID 273497
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:20]=[CH:19][C:18]([C:21]2([C:24]#[N:25])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C1C=CC(P([C:39]2[C:48]([C:49]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=[C:47]3[C:42]([CH:43]=CC=C3)=[CH:41][CH:40]=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:43][C:42]1[CH:41]=[CH:40][CH:39]=[C:48]([CH3:49])[C:47]=1[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH:10][C:15]3[CH:20]=[CH:19][C:18]([C:21]4([C:24]#[N:25])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:8]=[N:9][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 634876Binap, (A+-)-HCID 27952731-(4-Bromophenyl)CyclopropanecarbonitrileHCID 23665647Potassium tert-butoxideHCID 248227527-Bromo-5-methylbenzo[e][1,2,4]triazin-3-amine

Produkt 1

HCID 11603841HCID 11603841, VerbindungAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

About 50 mg (0.2 mmol) of 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine and about 84 mg (0.38 mmol) of 1-(4-bromo-phenyl)-cyclopropanecarbonitrile were dissolved in about 10 ml of toluene. About 8 mg (0.009 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 5 mg of 1-{4-[7-(2,6-dimethyl-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-phenyl}-cyclopropanecarbonitrile (product having formula (X)) was isolated. ESI-MS: [M+H]+, 406.5; 1H NMR (DMSO-d6): δ 1.49 (q, 2 H, J=5.3 Hz), 1.72 (q, 2 H, J=5.3 Hz), 2.05 (s, 6 H), 2.67(s, 3 H), 7.18 (d, J=7.4 Hz, 2 H), 7.23 (m, 1H), 7.38 (d, J=6.85 Hz, 2 H), 7.63 (s, 1 H), 7.91 (s, 1 H), 8.06 (d, J=6.85 Hz, 2 H).

Aufarbeitung

  1. customThe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2e41c16a65ae471f98daa834ef33cecc
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456176B2

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