Reaktion #1597411

Reaktionsgleichung

Water

tert-butyl {(1S)-1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl}carbamate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

potassium phosphate

→

tert-butyl[(1S)-1-benzyl-2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl]carbamate

Ausbeute 83.4%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with chloroform
2. 2
   WaschenThe separated organic layer was washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Sonstigeevaporated in vacuo
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

To a suspension of tert-butyl {(1S)-1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl}carbamate (1.0 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (587 mg) and potassium phosphate (1.52 g) in dimethoxyethane (30 mL) was added 1,1′-bis(diphenylphosphino)ferrocene palladium(II) chloride (58 mg) and the mixture was stirred at 120° C. for 4 hours. Water was added and the mixture was extracted with chloroform. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl[(1S)-1-benzyl-2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl]carbamate (830 mg).

Quelle