1-(1H-indol-2-yl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichloroethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0° and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reaction mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0° and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichloroethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0 and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reacton mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0 and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of SnCl4 (10 mL, 10.0 mmol) was added to a stirred solution of 5-bromoindole (ab) (980 mg, 5.0 mmol) and acetyl chloride (0.714 mL, 785 mg, 10.0 mmol) in 20 mL of dry toluene at 0° C. The resulting mixture was stirred at room temperature during 4 hours, and then 50 ml, of water was added. The mixture was extracted with EtOAc (3×20 mL) and the collected organic layers were washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under vacuum. Column chromatography using EtOAc-pentane (from 5/95 to 80/20) yielded pure acetylindole (jb) (1.0 g, 4.2 mmol) as a white solid. Yield: 84%. The mixture was extracted with EtOAc (3×20 mL) the collected organic layers were washed with water, brine dried over anhydrous MgSO4 filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichlorethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0° and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reaction mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0° and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 187 g (2 mols) N,N-dimethylmethyleneammonium chloride are suspended under an inert gas (nitrogen or argon) in 28 liters anhydrous acetonitrile. The stirred suspension is mixed with 159 g (1 mol) pulverized and dried 2-acetylindole, heated to the boil and, while stirring continuously, uniformly cooled over the course of 7 hours to 25° C. It is stirred overnight at 20°-25° C. The acetonitrile is substantially distilled off under vacuum and the remaining residue taken up in 20 liters of water and adjusted to pH 9-10 with concentrated ammonium hydroxide solution. This solution is stirred up three times with, in each case, 5 liters of dichloromethane. The organic phases are combined and washed with 5 liters of water. The organic phase is dried by the addition of anhydrous sodium sulphate, filtered and mixed with 5 liters tert-butyl methyl ether. The dichloromethane is substantially distilled off, the crystallization of the product thereby already commencing. This is completed by leaving to stand overnight at +4° C. The product is filtered off with suction, washed with n-hexane and dried under a vacuum. Yield: 141.7 g (65.6% of theory). The stirred suspension is mixed with 159 g (1 mol) uniformly cooled over the course of 7 hours to 25° C It is stirred overnight at 20°-25° C The acetonitrile is substantially distilled off under vacuum This solution is stirred up three times with, in each case, 5 liters of dichloromethane washed with 5 liters of water The organic phase is dried by the addition of anhydrous sodium sulphate filtered mixed with 5 liters tert-butyl methyl ether The dichloromethane is substantially distilled off the crystallization of the product by leaving The product is filtered off with suction washed with n-hexane dried under a vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichloroethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0° and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reaction mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0° and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichloroethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0 and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reacton mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0 and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 M solution of SnCl4 (10 mL, 10.0 mmol) was added to a stirred solution of 5-bromoindole (ab) (980 mg, 5.0 mmol) and acetyl chloride (0.714 mL, 785 mg, 10.0 mmol) in 20 mL of dry toluene at 0° C. The resulting mixture was stirred at room temperature during 4 hours, and then 50 ml, of water was added. The mixture was extracted with EtOAc (3×20 mL) and the collected organic layers were washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under vacuum. Column chromatography using EtOAc-pentane (from 5/95 to 80/20) yielded pure acetylindole (jb) (1.0 g, 4.2 mmol) as a white solid. Yield: 84%. The mixture was extracted with EtOAc (3×20 mL) the collected organic layers were washed with water, brine dried over anhydrous MgSO4 filtered concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichlorethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0° and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reaction mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0° and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 187 g (2 mols) N,N-dimethylmethyleneammonium chloride are suspended under an inert gas (nitrogen or argon) in 28 liters anhydrous acetonitrile. The stirred suspension is mixed with 159 g (1 mol) pulverized and dried 2-acetylindole, heated to the boil and, while stirring continuously, uniformly cooled over the course of 7 hours to 25° C. It is stirred overnight at 20°-25° C. The acetonitrile is substantially distilled off under vacuum and the remaining residue taken up in 20 liters of water and adjusted to pH 9-10 with concentrated ammonium hydroxide solution. This solution is stirred up three times with, in each case, 5 liters of dichloromethane. The organic phases are combined and washed with 5 liters of water. The organic phase is dried by the addition of anhydrous sodium sulphate, filtered and mixed with 5 liters tert-butyl methyl ether. The dichloromethane is substantially distilled off, the crystallization of the product thereby already commencing. This is completed by leaving to stand overnight at +4° C. The product is filtered off with suction, washed with n-hexane and dried under a vacuum. Yield: 141.7 g (65.6% of theory). The stirred suspension is mixed with 159 g (1 mol) uniformly cooled over the course of 7 hours to 25° C It is stirred overnight at 20°-25° C The acetonitrile is substantially distilled off under vacuum This solution is stirred up three times with, in each case, 5 liters of dichloromethane washed with 5 liters of water The organic phase is dried by the addition of anhydrous sodium sulphate filtered mixed with 5 liters tert-butyl methyl ether The dichloromethane is substantially distilled off the crystallization of the product by leaving The product is filtered off with suction washed with n-hexane dried under a vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This condensation reaction was studied in detail using the acetylindole (K5) and the indole (J6) using phosphoryl chloride as a condensing agent in 1,2-dichloroethane as solvent. A solution of acetylindole (K5) in 1,2-dichloroethane was cooled in an ice/salt bath and phosphoryl chloride was added slowly, keeping the temperature of the reaction mixture between 0° and 5° C. during the addition. This low temperature was preferred during the initial stages of this reaction to minimize the formation of unwanted byproducts. After 30 minutes stirring while the reaction mixture warmed to room temperature, indole (J6) in 1,2-dichloroethane was added. The reaction mixture was stirred overnight at room temperature and gas chromatographic analysis indicated that the condensation, though not complete, had taken place. The condensation reaction was driven to completion by refluxing the reaction mixture for one hour. The product, unsymmetrical indolylethene [Table 3, Entry 22], was isolated in good yield (74%, Example 11). This condensation reaction the temperature of the reaction mixture between 0° and 5° C. during the addition stages of this reaction The reaction mixture was stirred overnight at room temperature gas chromatographic analysis indicated that the condensation The condensation reaction by refluxing the reaction mixture for one hour