Potassium Carbonate → 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-(2-methylpropyl)imidazo[1,2-a]quinoxalin-4-amine

HRID 1025484Notizen

Reaktionsgleichung

Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[O:20]1[C:25]2[CH:26]=[CH:27][C:28](B(O)O)=[CH:29][C:24]=2[O:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:20]1[C:25]2[CH:26]=[CH:27][C:28]([C:2]3[N:6]4[C:7]5[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]4=[N:4][CH:3]=3)=[CH:11][CH:10]=[CH:9][CH:8]=5)=[CH:29][C:24]=2[O:23][CH2:22][CH2:21]1

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

0.1 mmol (1-bromo-imidazo[1,2-a]quinoxalin-4-yl)-isobutyl-amine (intermediate example 2.1, 1 mL, 0.1 M in NMP), 0.15 mmol 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid (0.3 mL, 0.5 M in NMP, 1.5 eq), 0.02 mmol Pd(dppf)Cl2 (0.533 mL, 0.0375M in NMP, 0.2 eq) and 0.3 mmol K2CO3 (0.3 mL, 1M in water, 3 eq) were combined in a sealed vial and heated at 130° C. under microwave irradiation for 60 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 8.1 mg (22%) 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-(2-methylpropyl)imidazo[1,2-a]quinoxalin-4-amine. UPLC-MS: RT==1.26 min; m/z (ES+) 375.4 [MH+]; required MW=374.4.

Aufarbeitung

temperatureAfter cooling
filtrationthe solution was filtered

Quellen und Nachweise

ORD-Eintrag: ord-d97bf9c4f1ec4398a05c3a21af71d2e1
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08729082B2

Notizen zur Reaktion

Wird geladen…