Реакция #979

Уравнение реакции

3-indolebutyric acid

N,N-diisopropylethylamine

N,N-dimethylhydroxylamine hydrochloride

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

→

amide

Выход 94.3%

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

Выход 94.3%

Растворители

acetonitrile

Условия реакции

Обработка

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

Методика

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.

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