Cesium carbonate → HCID 86684149, Verbindung

HRID 1024071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1024071
Br[C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=[C:4]([Cl:19])[CH:3]=1.[O:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]3[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=3)[CH2:26][CH2:25]2)[CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:19][C:4]1[CH:3]=[C:2]([NH:36][C:33]2[CH:32]=[CH:31][C:30]([N:27]3[CH2:28][CH2:29][N:24]([CH:22]4[CH2:21][O:20][CH2:23]4)[CH2:25][CH2:26]3)=[CH:35][N:34]=2)[C:10]2[N:9]=[CH:8][N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[CH:5]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866841255-(4-(Oxetan-3-yl)piperazin-1-yl)pyridin-2-amineHCID 866841484-Bromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole

Produkt 1

HCID 86684149HCID 86684149, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A microwave vial equipped with a magnetic stirrer was charged with 116a (600 mg, 1.65 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (390 mg 1.67 mmol), cesium carbonate (1.09 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium(0) (152 mg, 0.167 mmol), Xantphos (193 mg, 0.334 mmol), and dioxane (10 mL). After bubbling nitrogen through the suspension for 10 minutes, the reaction was heated at 120° C. overnight. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was washed with a mixed solvent of petroleum ether and ethyl acetate (15 mL, 2:1) to afford 116b as a yellow solid (720 mg, 85%). MS-ESI: [M+H]+ 515.2

Aufarbeitung

  1. customA microwave vial equipped with a magnetic stirrer
  2. customAfter bubbling nitrogen through the suspension for 10 minutes
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe residue was washed with a mixed solvent of petroleum ether and ethyl acetate (15 mL, 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-c23c489184a042f695691bb6e7ed2d12
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722676B2

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