Cesium carbonate → HCID 10162554, Verbindung

HRID 896082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896082
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]#[CH:36])[CH2:30][CH2:29]1.C([O-])([O-])=O.[Cs+].[Cs+].C(N(CC)C(C)C)(C)C>COCCOCCOC.CC(OC)(C)C.Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:6]2[CH:7]=[C:2]([C:36]#[C:35][CH2:34][N:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]3)[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])=[O:9])=[CH:11][CH:12]=1

Komponenten

10

Edukt 4

HCID 10796Cesium carbonateHCID 81531DiisopropylethylamineHCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineHCID 22349575(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone

Produkt 1

HCID 10162554HCID 10162554, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 8150DiglymeLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

(5-Bromo-2-methoxy-phenyl)-[4-(2,4-difluoro-phenylamino)-phenyl]-methanone (0.5 g; 1.18 mmol), 1-methyl-4-prop-2-ynyl-piperazine (0.33 g; 2.37 mmol), PdCl2(PPh3)2 (0.158 g; 0.22 mmol), Cs2CO3 (1.0 g; 3.1 mmol) and CuI (50 mg; 0.26 mmol) are dissolved in diethylene glycol dimethyl ether (10 ml) and N,N-diisopropylethylamine (5 ml) and heated to 140° C. for 1 hour. The reaction mixture is diluted with TBME, filtered, evaporated and purified by chromatography (SiO2, EtOAc/MeOH/NH3conc 100/0/0>90/10/1) to yield the crude title compound as brown foam. The latter is dissolved in 2N HCl, washed with EtOAc, Na2CO3 added to the aqueous phase and extracted with EtOAc. The organic phase is filtered through Alox and evaporated to give the pure product as yellow foam (177 mg; 32%).

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by chromatography (SiO2, EtOAc/MeOH/NH3conc 100/0/0>90/10/1)
  4. customto yield the crude title compound as brown foam
  5. washwashed with EtOAc, Na2CO3
  6. additionadded to the aqueous phase
  7. extractionextracted with EtOAc
  8. filtrationThe organic phase is filtered through Alox
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c4d1e256d6fb4a36ba975b88c3925956
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919336B2

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