Reacción #46775

Ecuación de reacción

NaOH

HCl

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

biphenyl-4-thiol

iodine

→

title compound

Rendimiento 37.8%

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

Rendimiento 37.8%

Disolventes

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Extracciónthe organics extracted with EtOAc
3. 3
   ExtracciónThe EtOAc extractions
4. 4
   Lavadowashed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated under reduced pressure
7. 7
   Otroto give crude material
8. 8
   OtroPurification

Procedimiento

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).

Fuente