Reaktion #61750

Reaktionsgleichung

5-bromo-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide

aniline

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

potassium tert-butoxide

→

5-Phenylamino-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide

Ausbeute 40.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was refluxed overnight
2. 2
   Einengenconcentrated
3. 3
   SonstigePurification of the dark brown residue by HPLC
4. 4
   Sonstigeafforded the product

Vorschrift

To a solution of 5-bromo-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide (1.0 mmol) in toluene (7.5 mL) was added aniline (1.3 mmol), tris(dibenzylidineacetone)dipalladium(0) (“Pd2dba”) (Aldrich) (0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (“BINAP”) (0.1 mmol), and potassium tert-butoxide (“t-BuOK”) (1.5 mmol), and the resulting mixture was refluxed overnight. The reaction was then cooled to room temperature, passed through a plug of silica and concentrated. Purification of the dark brown residue by HPLC afforded the product. Yield: 40%. MS: 362 (M+1).

Quelle