Réaction #979

Équation de réaction

3-indolebutyric acid

N,N-diisopropylethylamine

N,N-dimethylhydroxylamine hydrochloride

benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

→

amide

Rendement 94.3%

N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

Rendement 94.3%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Concentrationwas then concentrated to dryness
2. 2
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate
3. 3
   Lavagewashed with water, 0.5N HCl, saturated NaHCO3 and brine
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   LavageFlash chromatography (elution with a gradient of 2-10% ether in methylene chloride)

Mode opératoire

To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) and the resulting mixture was allowed to stir at room temperature overnight and was then concentrated to dryness. The residue was dissolved into ethyl acetate and washed with water, 0.5N HCl, saturated NaHCO3 and brine and then dried over MgSO4 and concentrated. Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride) provided 2.0 g of the amide 139. 1H NMR consistent with structure.

Source