Réaction #2487456

Équation de réaction

potassium carbonate

N-(2-bromo-5-chloro-4-methoxyphenyl)-2,2,2-trifluoroacetamide

phenylacetylene

triethylamine

→

title compound

6-Chloro-5-methoxy-2-phenyl-1H-indole

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   Températureto cool
3. 3
   workup.STIRRINGThe mixture was stirred at 120° C. for 2 more hours under microwave irradiation
4. 4
   workup.WAITThe reaction mixture was left
5. 5
   Températureto cool
6. 6
   Filtrationfiltered through Celite (registered trademark)
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   AutreThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

To a mixture of N-(2-bromo-5-chloro-4-methoxyphenyl)-2,2,2-trifluoroacetamide (512 mg), phenylacetylene (0.254 mL), copper(I) iodide (17.5 mg), triethylamine (0.549 mL), and acetonitrile (12.3 mL) was added bis(triphenylphosphine) palladium(II) dichloride (32.5 mg). The mixture was stirred at 120° C. for 2 hours under microwave irradiation. The reaction mixture was left to cool. To the reaction mixture was added potassium carbonate (532 mg). The mixture was stirred at 120° C. for 2 more hours under microwave irradiation. The reaction mixture was left to cool, and filtered through Celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (255 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 6.70-6.80 (1H, m), 7.13 (1H, s), 7.30-7.50 (4H, m), 7.60-7.70 (2H, m), 8.00-8.40 (1H, br).

Source