Potassium Carbonate → HCID 68559071, Verbindung

HRID 2382094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382094
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH:16]=[CH2:17])[C:8]1[C:9](Cl)=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:16]([CH3:17])=[CH:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:16](=[CH2:17])[CH2:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 2

HCID 11430Potassium CarbonateHCID 86639381HCID 86639381, Verbindung

Produkt 2

HCID 68559040HCID 68559040, VerbindungHCID 68559071HCID 68559071, VerbindungAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of allyl-(2-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (8.03 g, 30 mmol), tetrabutylammonium chloride (9.4 g, 30 mmol), palladium acetate (673 mg, 3 mmol) and potassium carbonate (12.4 g, 3 mmol) in DMF (300 mL) is heated at 80° C. for 1.5 h. The reaction is quenched with DCM and washed with water. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford 3-methyl-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester and 3-methylene-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester (1.58 g).

Aufarbeitung

  1. customThe reaction is quenched with DCM
  2. washwashed with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-8cb00e3b22144a6ea880c96824089970
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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