Réaction #2487469

Équation de réaction

1-(2-amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol

potassium carbonate

2-bromomesitylene

N,N-dimethylformamide

→

title compound

Rendement 92.6%

2-(Butan-2-yl)-6-chloro-5-methoxy-1H-indole

Rendement 92.6%

Solvants

water

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autreto separate the organic layer
2. 2
   LavageThe organic layer was washed with saturated brine
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

A mixture of 1-(2-amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol (602 mg), tetrakis(triphenylphosphine) palladium(0) (135 mg), potassium carbonate (646 mg), 2-bromomesitylene (0.420 mL), and N,N-dimethylformamide (11.7 mL) was stirred at 160° C. for 1 hour under microwave irradiation. To the reaction mixture were added ethyl acetate and water to separate the organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (514 mg). 1H-NMR (CDCl3) δ ppm: 0.91 (3H, t, J=7.4 Hz), 1.32 (3H, d, J=6.8 Hz), 1.55-1.80 (2H, m), 2.70-2.90 (1H, m), 3.91 (3H, s), 6.10-6.20 (1H, m), 7.05 (1H, s), 7.25-7.35 (1H, m), 7.50-8.00 (1H, br).

Source