5-methoxy-1H-indol-6-ol

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

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy-5-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 19 (white powder, 30% yield) are obtained. to reflux for 16 hours under nitrogen After the mixture is cooled 30 g of silica 60 are added to the reaction medium the mixture is filtered the filtrate concentrated two-fold The white precipitate obtained is filtered off recrystallized again in 30 ml of toluene After being dried under vacuum, 4.2 g of the derivative 19 (white powder, 30% yield) are obtained

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy 5-methoxy indole and 12.95 g (0.147 mole) of formyl acetic anhydride in 100 ml toluene is refluxed for 16 hours under nitrogen atmosphere. After cooling, 30 g of silica 60 is added to the reacting medium, and it is filtered and concentrated to half its volume. The white precipitate that is obtained is filtered and then recrystallized in 30 ml toluene. After vacuum-drying, 4.2 g of 6-formyloxy 5-methoxy indole is obtained (white powder, yield 30%). After cooling 30 g of silica 60 is added to the reacting medium, and it is filtered concentrated to half its volume The white precipitate that is obtained is filtered recrystallized in 30 ml toluene After vacuum-drying

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Hydroxy-5-methoxyindole (2 g; 0.0123 mole) dissolved in 10 ml of dimethylformamide (DMF) is introduced dropwise in the course of 20 minutes into a mixture of 1-bromohexadecane (4.5 g; 0.0148 mole) and potassium carbonate (1.87 g; 0.0135 mole) in 45 ml of DMF at 70° C. and under nitrogen. The reaction mixture is stirred under nitrogen at 80° C. for 3 and a half hours. The blackish mixture is poured into ice-cold water with stirring and the brownish solid formed is immediately filtered off and washed with water. It is taken up in dichloromethane and dried over sodium sulphate. After chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane, the derivative 26 is obtained (1.66 g; 35% yield). The blackish mixture is poured into ice-cold water with stirring the brownish solid formed is immediately filtered off washed with water dried over sodium sulphate After chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane the derivative 26 is obtained (1.66 g; 35% yield)

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy-5-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained. to reflux for 16 hours under nitrogen After the mixture is cooled 30 g of silica 60 are added to the reaction medium the mixture is filtered the filtrate concentrated two-fold The white precipitate obtained is filtered off recrystallized again in 30 ml of toluene After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy-5-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained. to reflux for 16 hours under nitrogen After the mixture is cooled 30 g of silica 60 are added to the reaction medium the mixture is filtered the filtrate concentrated two-fold The white precipitate obtained is filtered off recrystallized again in 30 ml of toluene After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy 5-methoxy indole and 12.95 g (0.147 mole) of formyl acetic anhydride in 100 ml toluene is refluxed for 16 hours under nitrogen atmosphere. After cooling, 30 g of silica 60 is added to the reacting medium, and it is filtered and concentrated to half its volume. The white precipitate that is obtained is filtered and then recrystallized in 30 ml toluene. After vacuum-drying, 4.2 g of 6-formyloxy 5-methoxy indole is obtained (white powder, yield 30%). After cooling 30 g of silica 60 is added to the reacting medium, and it is filtered concentrated to half its volume The white precipitate that is obtained is filtered recrystallized in 30 ml toluene After vacuum-drying

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of sodium hydride (0.94 g, 19.6 mmol of a 50% oil dispersion) in dimethylformamide (20 ml) under nitrogen and cooled to -5° C. was added, dropwise, 5-methoxy-6-hydroxyindole (3.2 g, 19.6 mmol) dissolved in dimethylformamide (60 ml) so that the temperature did not exceed -2° C. After complete addition, the reaction was stirred for 45 minutes at 0° C. While maintaining the reaction temperature between -5° C. and 0° C., a solution of 1-bromo-3-chloropropane (3.1 g, 19.6 mmol) dissolved in dimethylformamide (15 ml) was slowly added. The mixture was stirred at ambient temperature under nitrogen for 21 hours. The reaction was cooled in an ice bath, and water was added to destroy the excess sodium hydride, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried with MgSO4 and concentrated to yield 5.3 g of a dark, oily liquid. This was combined with an additional sample, for a total of 10.0 g, and purification by preparative HPLC (Waters Associates prep LC/System 500) provided 5.1 g of a brown solid. A 2.5 g sample was recrystallized from isopropyl alcohol to yield 1.1 g (30%) of 6-(3-chloropropoxy)o5-methoxyindole as beige crystals, m.p.=73°-75° C. was added did not exceed -2° C After complete addition While maintaining the reaction temperature between -5° C. and 0° C. was slowly added The mixture was stirred at ambient temperature under nitrogen for 21 hours The reaction was cooled in an ice bath to destroy the excess sodium hydride the aqueous mixture was extracted with ethyl acetate The ethyl acetate extract was washed with water dried with MgSO4 concentrated to yield 5.3 g of a dark, oily liquid This was combined with an additional sample, for a total of 10.0 g, and purification by preparative HPLC (Waters Associates prep LC/System 500)

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy-5-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 19 (white powder, 30% yield) are obtained. to reflux for 16 hours under nitrogen After the mixture is cooled 30 g of silica 60 are added to the reaction medium the mixture is filtered the filtrate concentrated two-fold The white precipitate obtained is filtered off recrystallized again in 30 ml of toluene After being dried under vacuum, 4.2 g of the derivative 19 (white powder, 30% yield) are obtained

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Hydroxy-5-methoxyindole (2 g; 0.0123 mole) dissolved in 10 ml of dimethylformamide (DMF) is introduced dropwise in the course of 20 minutes into a mixture of 1-bromohexadecane (4.5 g; 0.0148 mole) and potassium carbonate (1.87 g; 0.0135 mole) in 45 ml of DMF at 70° C. and under nitrogen. The reaction mixture is stirred under nitrogen at 80° C. for 3 and a half hours. The blackish mixture is poured into ice-cold water with stirring and the brownish solid formed is immediately filtered off and washed with water. It is taken up in dichloromethane and dried over sodium sulphate. After chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane, the derivative 26 is obtained (1.66 g; 35% yield). The blackish mixture is poured into ice-cold water with stirring the brownish solid formed is immediately filtered off washed with water dried over sodium sulphate After chromatography on silica 60 (eluent: toluene/CH2Cl2, 50:50), and recrystallization in hexane the derivative 26 is obtained (1.66 g; 35% yield)

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

Procedure: A solution of 12 g (0.0735 mole) of 6-hydroxy-5-methoxyindole and 12.95 g (0.147 mole) of acetic formic anhydride in 100 ml of toluene is brought to reflux for 16 hours under nitrogen. After the mixture is cooled, 30 g of silica 60 are added to the reaction medium, the mixture is filtered and the filtrate concentrated two-fold. The white precipitate obtained is filtered off and then recrystallized again in 30 ml of toluene. After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained. to reflux for 16 hours under nitrogen After the mixture is cooled 30 g of silica 60 are added to the reaction medium the mixture is filtered the filtrate concentrated two-fold The white precipitate obtained is filtered off recrystallized again in 30 ml of toluene After being dried under vacuum, 4.2 g of the derivative 8 (white powder, 30% yield) are obtained