Reaction #2487456

Reaction equation

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   Temperatureto 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
   Temperatureto cool
6. 6
   Filtrationfiltered through Celite (registered trademark)
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   OtherThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Procedure

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