Synthesis of 5-acylindoles via regioselective acylation of 3-trifluoroacetylindole

Synlett

Volumn , Issue 10, 2003, Pages 1447-1450

  Li, Jun ^a,b   Li, Bogang ^a   Chen, Xiaozhen ^a   Zhang, Guolin ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

3 trifluoroacetylindole; 5 acylindole; 5 acylindole 3 carboxylic acid; Acylation; Regioselectivity

Indexed keywords

3 TRIFLUOROACETYLINDOLE; CHLORINE DERIVATIVE; INDOLE DERIVATIVE; LEWIS ACID; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CELL LINE; CYTOTOXICITY; DECARBOXYLATION; DEPROTECTION REACTION; DRUG ACTIVITY; DRUG HYDROLYSIS; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0042889520     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40864     Document Type: Article

References (22)

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16. 3 solution (three times) and NaCl solution(twice).
17. Acylated Indole Compounds: A mixture of 5-acetyl-3-trifluoroacetylindole (3a) and 6-acetyl-3-trifluoroacetylindole (4a) (72:28) was obtained by chromatography in total yield 85%. Recrystallization of the mixture from EtOAc resulted in pure 3a, but pure 4a could not be obtained.
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20. 3).
21. Hydrolysis of 3a, 3c-f; General Procedure: To a aq 4.4 M KOH solution was added 5-acyl-3-trifluoroacetylindole (3a, 3c-f, 1 mmol). The mixture was refluxed until 3 disappeared (0.5-2 h). The mixture was adjusted to pH = 5-6 with 5.5 M HCl(aq) to precipitate carboxylic acid, which was extracted with EtOAc or n-butanol (3 x 20 mL).
22. 2) occurred and kept at this temperature until gas evolution ceased (45-120 min).