Cesium carbonate → 1-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester

HRID 1748567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748567
[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]([C:22]1[CH:23]=[CH:24][C:25](Br)=[N:26][CH:27]=1)(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([C:25]2[CH:24]=[CH:23][C:22]([C:19](=[O:21])[CH3:20])=[CH:27][N:26]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 11171190tert-butyl 1H-pyrrole-3-carboxylateHCID 156681955-Acetyl-2-bromopyridine

Produkt 1

HCID 866925131-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl esterAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 1H-pyrrole-3-carboxylic acid tert-butyl ester (700 mg) described in Reference Example 50, 1,1′-bis(diphenylphosphino)ferrocene (35 mg), palladium acetate (9.4 mg), cesium carbonate (1.64 g) and 5-acetyl-2-bromopyridine (921 mg) in toluene (10 ml) was stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, ice water was added thereto, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(5-acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester (380 mg) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d1ca1a8a6f3549d399ab335850cd181f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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