Cesium carbonate → 2-Butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-one

HRID 1878634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1878634
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:27])[CH:24]=2)[C:19]1=[O:28])[CH2:15][CH2:16][CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]I.C(OCC)(=O)C.O>[CH2:14]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:27][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][C:7]=3[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:24]=2)[C:19]1=[O:28])[CH2:15][CH2:16][CH3:17]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 27629283-Bromo-4-phenylpyridineHCID 138973842-Butyl-5-hydroxyisoindolin-1-one

Produkt 1

HCID 534772442-Butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-oneAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

A mixture of 3-bromo-4-phenylpyridine (50 mg, 0.213 mmol), 2-butyl-5-hydroxy-isoindolin-1-one (88 mg, 0.427 mmol), Cs2CO3 (139 mg, 0.427 mmol), CuI (16.3 mg, 0.085 mmol) and 2,2,6,6-tetramethyl-3.5-heptanedione (53 μL, 0.256 mmol) in degassed N-methylpyrrolidone (NMP) (2 mL) was stirred and heated in the microwave (220° C., 300 W, 30 min). Two of those reactions were combined, excess water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were extracted with aqueous HCl (2 M) and the combined extracts were basified with aqueous NaOH (2 M) followed by extraction with ethyl acetate. The combined organic layers were washed with water and dried over MgSO4. Purification by HPLC provided 2-butyl-5-(4-phenylpyridin-3-yloxy)isoindolin-1-one (16 mg, 8%).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with aqueous HCl (2 M)
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1db14dfe5fcf4e5595c7e889eae89bac
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314120B2

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