반응 #2487456

반응 방정식

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

용매

acetonitrile

반응 조건

후처리

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

실험 절차

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).

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