Reaktion #68427

Reaktionsgleichung

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

Compound 172

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

2-pyrrolidinone

POCl3

→

title compound

1-Benzyl-N-(3,4-difluorobenzyl)-6-(3,4-dihydro-2H-pyrrol-5-ylamino)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide

Lösungsmittel

EtOAc

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas cooled to room temperature
2. 2
   Waschenwashed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by reverse phase chromatography on C18 bonded silica gel (MeOH)

Vorschrift

A mixture of 2-pyrrolidinone (47 mg, 0.55 mmol) and POCl3 (0.10 ml, 1.1 mmol) was stirred at 0° C. to room temperature for 2h. To the above mixture was then added a solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-2-isopropyl-1H-indole-3-carboxamide (Compound 172, 50 mg, 0.11 mmol) in toluene (3 ml). The reaction was heated to 110° C. for 16 h and was cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by reverse phase chromatography on C18 bonded silica gel (MeOH) to yield the title compound as a white solid.

Quelle