2-(furan-2-yl)aniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 4-cyano-3-methylbenzoic acid from Example C (187 mg, 1.16 mmol) in toluene (10 ml) was added thionyl chloride (425 μl, 5.8 mmol). The mixture was heated at reflux for 2 h, cooled, evaporated in vacuo and azeotroped with toluene. The residue was taken up in CH2Cl2 (5.0 ml) and added to a solution of 2-furan-2-yl-phenylamine from Example 21A (185 mg, 1.16 mmol) and triethylamine (324 μl, 2.32 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 18 h, partitioned between water and chloroform and separated. The organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid; yellow solid 233 mg, 66%. The mixture was heated at reflux for 2 h cooled evaporated in vacuo azeotroped with toluene partitioned between water and chloroform separated The organic layers were dried evaporated in vacuo The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid

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

Procedure: To a solution of 2-bromoaniline (137 mg, 0.80 mmol) in THF (4.0 ml) was added 2-furanboronic acid (89 mg, 0.80 mmol), tetrakis-(triphenylphosphine)palladium (0) (92 mg, 0.08 mmol) and sodium carbonate solution (2M, 2.0 ml, 4.0 mmol). The mixture was heated in a sealed tube using a microwave reactor (20 W) at 130° C. for 25 min. This procedure was carried out 5 times and the reaction mixtures were combined. The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil; yield 211 mg, 33%. The mixture was heated in a sealed tube at 130° C. for 25 min the reaction mixtures The mixture was separated the aqueous layer extracted with EtOAc The combined organic layers were dried evaporated in vacuo The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil

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

Procedure: To a solution of 2-bromoaniline (137 mg, 0.80 mmol) in THF (4.0 ml) was added 2-furanboronic acid (89 mg, 0.80 mmol), tetrakis-(triphenylphosphine)palladium (0) (92 mg, 0.08 mmol) and sodium carbonate solution (2M, 2.0 ml, 4.0 mmol). The mixture was heated in a sealed tube using a microwave reactor (20 W) at 130° C. for 25 min. This procedure was carried out 5 times and the reaction mixtures were combined. The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil; yield 211 mg, 33%. The mixture was heated in a sealed tube at 130° C. for 25 min the reaction mixtures The mixture was separated the aqueous layer extracted with EtOAc The combined organic layers were dried evaporated in vacuo The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil

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

Procedure: 2-(2-Nitrophenyl)furan (0.51 g) was dissolved in 10 mL of EtOH. To this solution was added 0.07 g of 10% Pd/C and 1 mL of EtOH. This mixture was stirred and treated dropwise with 1.4 mL of 35% hydrazine. The suspension was filtered, and the filtrate was evaporated. The resulting residue was taken up in 50 mL of toluene and re-evaporated to give 2-(2-aminophenyl)furan. [This compound was reported in Smith et al.; J. Am. Chem Soc. 1953, 75, 6335.] The suspension was filtered the filtrate was evaporated re-evaporated

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

Procedure: 113 mg (0.6 mmol) 2-(2-nitro-phenyl)-furan are dissolved in 2 ml of ethanol and combined with 6 mg palladium on activated charcoal (10% Pd). 110 μl of a 35% aqueous hydrazine solution are added to this suspension and the reaction mixture is stirred for 20 h under reflux conditions. The catalyst is suction filtered, the filtrate is combined with 25 ml of water and adjusted to pH 5. This mixture is extracted three times with 10 ml of ethyl acetate. The combined organic phases are dried and the solvent is eliminated in vacuo. filtered This mixture is extracted three times with 10 ml of ethyl acetate The combined organic phases are dried

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

Procedure: To a solution of 4-cyano-3-methylbenzoic acid from Example C (187 mg, 1.16 mmol) in toluene (10 ml) was added thionyl chloride (425 μl, 5.8 mmol). The mixture was heated at reflux for 2 h, cooled, evaporated in vacuo and azeotroped with toluene. The residue was taken up in CH2Cl2 (5.0 ml) and added to a solution of 2-furan-2-yl-phenylamine from Example 21A (185 mg, 1.16 mmol) and triethylamine (324 μl, 2.32 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 18 h, partitioned between water and chloroform and separated. The organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid; yellow solid 233 mg, 66%. The mixture was heated at reflux for 2 h cooled evaporated in vacuo azeotroped with toluene partitioned between water and chloroform separated The organic layers were dried evaporated in vacuo The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid

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

Procedure: To a solution of 2-bromoaniline (137 mg, 0.80 mmol) in THF (4.0 ml) was added 2-furanboronic acid (89 mg, 0.80 mmol), tetrakis-(triphenylphosphine)palladium (0) (92 mg, 0.08 mmol) and sodium carbonate solution (2M, 2.0 ml, 4.0 mmol). The mixture was heated in a sealed tube using a microwave reactor (20 W) at 130° C. for 25 min. This procedure was carried out 5 times and the reaction mixtures were combined. The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil; yield 211 mg, 33%. The mixture was heated in a sealed tube at 130° C. for 25 min the reaction mixtures The mixture was separated the aqueous layer extracted with EtOAc The combined organic layers were dried evaporated in vacuo The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil