Reaktion #44893

Reaktionsgleichung

NaOH

2-Methyl-2,3-dihydro-benzoisothiazole

ethyl acetate methanol triethylamine

indole

Tricloroacetic acid

→

[2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine

Ausbeute 67.0%

Lösungsmittel

THF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionExtraction
2. 2
   Sonstigewith ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

Vorschrift

2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine (67% yield).

Quelle