4-ethoxy-1H-indole

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An oven dried two neck flask was charged with 5 ml DMF and NaH (66 mg, 60% in oil, 1.65 mmol). The mixture was cooled down to 0° C., followed by dropwise addition of 4-hydroxy indole (200 mg, 1.5 mmol) in 5 ml DMF over 10 second. After stirring for 30 min under N2, bromoethane in 2 ml DMF was added dropwise, and the reaction was allowed to warm to rt. with continued stirring for 2 hr. Removal of the solvent in vacuo, followed by aqueous work up afforded crude 4-ethoxyindole which was purified by prep. HPLC to afford 201 mg (83%) of pure 4-ethxyindole; HPLC retention time, 1.190 min. An oven dried two neck flask to warm to rt with continued stirring for 2 hr Removal of the solvent in vacuo

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

Procedure: 4-Hydroxyindole (1.0 equivalents) is dissolved in dry, degassed acetone. EtBr (5.0 equivalents) and Cs2CO3 (2.5 equivalents) are added, and the resulting solution is stirred for 18 hours. The reaction mixture is filtered through a Celite plug. The solvent is evaporated, and the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95) to yield the title compound. in dry degassed acetone The reaction mixture is filtered through a Celite plug The solvent is evaporated the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95)

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

Procedure: 4-Hydroxyindole (1.0 equivalents) is dissolved in dry, degassed acetone. EtBr (5.0 equivalents) and Cs2CO3 (2.5 equivalents) are added, and the resulting solution is stirred for 18 hours. The reaction mixture is filtered through a Celite plug. The solvent is evaporated, and the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95) to yield the title compound. in dry degassed acetone The reaction mixture is filtered through a Celite plug The solvent is evaporated the product is purified by flash chromatography (MeOH:CH2Cl2, 5:95)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An oven dried two neck flask was charged with 5 ml DMF and NaH (66 mg, 60% in oil, 1.65 mmol). The mixture was cooled down to 0° C., followed by dropwise addition of 4-hydroxy indole (200 mg, 1.5 mmol) in 5 ml DMF over 10 second. After stirring for 30 min under N2, bromoethane in 2 ml DMF was added dropwise, and the reaction was allowed to warm to rt. with continued stirring for 2 hr. Removal of the solvent in vacuo, followed by aqueous work up afforded crude 4-ethoxyindole which was purified by prep. HPLC to afford 201 mg (83%) of pure 4-ethxyindole; HPLC retention time, 1.190 min. An oven dried two neck flask to warm to rt with continued stirring for 2 hr Removal of the solvent in vacuo