Реакция #66712

Уравнение реакции

5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid

HCl

→

5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole

Выход 53.0%

Растворители

EtOAc

quinoline

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   Температураto reflux for 1.5 hours
3. 3
   Температураthe reaction mixture was refluxed for 1 hour
4. 4
   ТемператураThe reaction mixture was cooled
5. 5
   Экстракцияextracted with EtOAc
6. 6
   ПромывкаThe combined organic layers were washed with brine
7. 7
   Сушкаdried over magnesium sulfate
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated under reduced pressure
10. 10
    ДругоеThe residue was chromatographed (10% EtOAc/Hexanes)

Методика

To a solution of 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole-2-carboxylic acid (2.0 g, 7 mmol) in 5 ml quinoline was added copper powder (50 mg), and the reaction mixture was heated to reflux for 1.5 hours. Copper powder (50 mg) was added, and the reaction mixture was refluxed for 1 hour. The reaction mixture was cooled, diluted with EtOAc, poured into 50 ml 6 N HCl, and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (10% EtOAc/Hexanes) to give 5-Methoxy-3-methyl-6-trifluoromethyl-1H-indole (850 mg, 51%) as a solid.

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