Reaktion #46775

Reaktionsgleichung

NaOH

HCl

(4-acetylamino-2-methyl-indol-1-yl)-acetic acid ethyl ester

biphenyl-4-thiol

iodine

→

title compound

Ausbeute 37.8%

[4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic acid

Ausbeute 37.8%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionthe organics extracted with EtOAc
3. 3
   ExtraktionThe EtOAc extractions
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   Sonstigeto give crude material
8. 8
   SonstigePurification

Vorschrift

To a solution of (4-acetylamino-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.27 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight 1M NaOH (3 ml) was added and the reaction stirred at RT for a further 12 hours. The reaction was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.16 g).

Quelle