Réaction #11501

Équation de réaction

carbon monoxide

2-methyl-4-trifluoromethanesulfoxyindole

1-(4-(2-Propyloxyethoxy)benzoyl)-2-methylindole-4-acetic acid

N,N-dimethylformamide

triethylamine

→

title compound

2-Methylindole-4-carboxylic acid methyl ester

Solvants

ethyl acetate

water

methanol

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted
2. 2
   ExtractionThe aqueous layer was extracted with ethyl acetate
3. 3
   LavageThe combined organic layer was washed with water
4. 4
   Séchagea saturated aqueous solution of sodium chloride, successively, dried
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate)

Mode opératoire

To a solution of 2-methyl-4-trifluoromethanesulfoxyindole (6.32 g; prepared in Reference Example 1) in methanol (33.43 ml)-N,N-dimethylformamide (200 ml) was added triethylamine (6.3 ml) and tetrakis(triphenylphosphine)palladium (2.6 g). The inside of the vessel was replaced with carbon monoxide and the mixture was stirred at 60° C. overnight. After the reaction was completed, to the mixture was added water and ethyl acetate and then the mixture was extracted. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give the title compound (4.29 g) having the following physical data.

Source