Compound 1 (146.1mg; 0.7036mmol), phenylacetylene (232lL; 1.043mmol), Cl2Pd(dppf) (27.1mg; 0.0332mmol), LiCl (30.4mg; 0.717mmol), and Na2CO3 (136.8mg; 1.291mmol) were dissolved in DMF (4.0mL) and then a stream of N2 was passed through for 10min. The reaction mixture was then heated at 100 C for 3h, cooled to rt, and diluted with H2O. The mixture was extracted with EtOAc and then the organic extracts were washed with brine, dried (Na2SO4), and concentrated. The residue was purified by column chromatography (10g pre-packed column from ISCO, 50% heptane–EtOAc eluent) to yield 118.5mg (0.4715mmol; 67%) of 6-phenyl-5H-pyrrolo[2,3-b]pyrazine, compound 2
Cyclization of Amino(2-ethoxyetheny1)pyridines to 1H-Pyrrolopyridines (General Procedure): A mixture of an amino- (4) (2.5 mmol) and conc. HCI (0.5 ml) in MeOH (10 ml) was refluxed for 1-2 h. After evaporation of the solvent, the residue was basified with solid K2C03 and extracted with CHCI3. The CHCI3 extract was dried over MgSO4. The crude product obtained from the CHCl3 extract was purified by recrystallization.
Synthesis of 7-Azaindoles. General Procedure. Method A. The epoxide and the amine (1-2 equiv) were dissolved in 1-butanol ( mL/mmol epoxide), and the mixture was heated for the given reaction time to 110 °C (higher temperatures were achieved in sealed pressure tubes). The solvent was evaporated, the residue was treated with ethanol (3 mL/mmol epoxide), and concentrated hydrochloric acid (1 mL) was added. The reaction was stirred overnight, then diluted with water, basified with diluted NaOH solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel or by HPLC.
A new, mild, and efficient method for the synthesis of polyfunctionalized indoles by direct reaction of substituted 2-chloroanilines with cyclic or acyclic ketones was developed. This procedure is simple to carry out and broadly applicable.
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