Water → 8-(Benzyloxy)-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline

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Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](Cl)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][N:28]2[CH:31]=[CH:32][N:33]=[C:27]2[CH:26]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1.O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:31]1[N:28]3[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][O:21][CH3:20])=[CH:26][C:27]3=[N:33][CH:32]=1)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

8-(Benzyloxy)-2-chloroquinoline (5.0 g, 18.5 mmol), 7-(2-methoxyethoxy)-imidazo[1,2-a]pyridine (3.56 g, 18.5 mmol), Pd(PPh3)4 (1.07 g, 0.927 mmol), K2CO3 (5.12 g, 37.1 mmol), and Pd(OAc)2 (0.208 g, 0.927 mmol) were added to dioxane (74.1 ml, 18.5 mmol) and water (0.735 ml, 40.8 mmol) and the reaction mixture was heated to 100° C. overnight under nitrogen. The reaction was diluted with DCM and 5 g of carbon were added followed by filtration. The slurry was concentrated and the filtrate was triturated with 1:1 EtOAc/MTBE (30 mL). The resulting solids were stirred for 5 hours and then filtered to isolate the desired product as a solid (5.4 g, 69% yield).

Aufarbeitung

additionwere added
filtrationfollowed by filtration
concentrationThe slurry was concentrated
customthe filtrate was triturated with 1:1 EtOAc/MTBE (30 mL)
filtrationfiltered

Quellen und Nachweise

ORD-Eintrag: ord-84c16d0e761f49c1b8643adc94449a7d
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08138181B2

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