Cesium carbonate → 2-Butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one

HRID 1878633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878633
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5]2.[C:16]1([C:22]2[CH:23]=[C:24]([NH2:28])[CH:25]=[N:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:28][C:24]3[CH:25]=[N:26][CH:27]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:23]=3)[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 27629015-Phenylpyridin-3-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67432057HCID 67432057, Verbindung

Produkt 1

HCID 534771302-Butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-oneAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

5-Bromo-2-butylisoindolin-1-one (71.6 mg, 0.267 mmol), 5-phenylpyridin-3-amine (50.0 mg, 0.294 mmol) and Cs2CO3 (217.0 mg, 0.668 mmol) were added to suspension of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos) (12.7 mg, 0.027 mmol) and palladium acetate (PdOAc2) (8.0 mg, 0.040 mmol) in toluene (2 mL). The mixture was stirred and heated in the microwave (120° C., 300 W, 60 min). Water and ethyl acetate were added. The organic layer was separated, the aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4. Purification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol) provided 2-butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one (53 mg, 54%). ESI-MS [M+H]+=358.1.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customPurification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-6d499d031d8c4330b99d9c7f12944549
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314120B2

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