1H-indol-3-yl acetate

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

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

Procedure: Methanol (25 mL) was vigorously stirred under nitrogen for 20 min and then 7-fluoroisatin (IIIa) (150 mg, 0.91 mmol) and 3-acetoxyindole (106 mg, 0.61 mmol) were added and stirring was Continued for 5 min. Anhydrous Na2CO3 (155 mg) was added and the stirring was continued for 3 h. The dark precipitate was filtered and washed with aqueous methanol (1:1, 20 mL) to give 7 (130 mg, 0.46 mmol, 77%) selectively in a Z form. 1H NMR (DMSO, 400 MHz, δ ppm, J in Hz) 11.37 (1H, s, N′—H), 11.12 (1H, s, N—H), 8.58 (1H, d, J=7.7 Hz, H-4), 7.64 (1H, d, J=7.5 Hz, H-4′), 7.57 (1H, t, J=7.5 Hz H-6′), 7.42 (1H, d, J=7.5 Hz, H-7′), 7.15 (1H, t, J=8.0 Hz, H-5), 7.02 (2H, m, H-5′, 6); CI-MS m/z 281 (M+H)+. Anal. (C16H9N2O2F) C, H, N. the stirring was continued for 3 h The dark precipitate was filtered washed with aqueous methanol (1:1, 20 mL)

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

Procedure: Methanol (25 mL) was vigorously stirred under nitrogen for 20 min and then 7-fluoroisatin (IIIa) (150 mg, 0.91 mmol) and 3-acetoxyindole (106 mg, 0.61 mmol) were added and stirring was Continued for 5 min. Anhydrous Na2CO3 (155 mg) was added and the stirring was continued for 3 h. The dark precipitate was filtered and washed with aqueous methanol (1:1, 20 mL) to give 7 (130 mg, 0.46 mmol, 77%) selectively in a Z form. 1H NMR (DMSO, 400 MHz, δ ppm, J in Hz) 11.37 (1H, s, N′—H), 11.12 (1H, s, N—H), 8.58 (1H, d, J=7.7 Hz, H-4), 7.64 (1H, d, J=7.5 Hz, H-4′), 7.57 (1H, t, J=7.5 Hz H-6′), 7.42 (1H, d, J=7.5 Hz, H-7′), 7.15 (1H, t, J=8.0 Hz, H-5), 7.02 (2H, m, H-5′, 6); CI-MS m/z 281 (M+H)+. Anal. (C16H9N2O2F) C, H, N. the stirring was continued for 3 h The dark precipitate was filtered washed with aqueous methanol (1:1, 20 mL)

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

Procedure: Into a 500 mL round bottom flask was placed a solution of 1H-indol-3-yl acetate (8 g, 45.69 mmol) in tetrahydrofuran (150 mL). To this was added acetic anhydride (46.6 g, 456.86 mmol). Addition of triethylamine (9.25 g, 91.49 mmol) was next. To the mixture was added DMAP (1.11 g, 9.10 mmol). The resulting solution was allowed to react, with stirring, for 3 hours while the temperature was maintained at reflux in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 300 mL of ethyl acetate The resulting mixture was washed 2 times with 150 mL of NaCl(aq.). The mixture was dried over Na2SO4. The residue was purified by eluting through a column with a 20:1 petroleum ether/ethyl acetate solvent system. This resulted in 6.6 g (67%) of 1-acetyl-1H-indol-3-yl acetate as a white solid. Into a 500 mL round bottom flask was placed to react was maintained at reflux in a bath of oil The mixture was concentrated by evaporation under vacuum a rotary evaporator The resulting solution was diluted with 300 mL of ethyl acetate The resulting mixture was washed 2 times with 150 mL of NaCl(aq.) The mixture was dried over Na2SO4 The residue was purified by eluting through a column with a 20:1 petroleum ether/ethyl acetate solvent system This resulted in 6.6 g (67%) of 1-acetyl-1H-indol-3-yl acetate as a white solid

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 mL round bottom flask was placed a solution of 3-iodo-1H-indole (23 g, 94.65 mmol) in acetic acid (300 mL). To the mixture was added CH3COOAg (31.6 g, 189.22 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at 90° C. in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was dissolved with 100 mL of ethyl acetate. The resulting mixture was washed 2 times with 100 mL of NaCl(aq.). The final product was purified by recrystallization from MeOH/H2O in the ratio 2:3. This resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid. Into a 500 mL round bottom flask was placed To the mixture was added CH3COOAg (31.6 g, 189.22 mmol) to react A filtration The filtrate was concentrated by evaporation under vacuum a rotary evaporator The resulting solution was dissolved with 100 mL of ethyl acetate The resulting mixture was washed 2 times with 100 mL of NaCl(aq.) The final product was purified by recrystallization from MeOH/H2O in the ratio 2:3 This resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 500 mL round bottom flask was placed a solution of 3-iodo-1H-indole (23 g, 94.65 mmol) in acetic acid (300 mL). To the mixture was added CH3COOAg (31.6 g, 189.22 mmol). The resulting solution was allowed to react, with stirring, for 1 hour while the temperature was maintained at 90° C. in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). A filtration was performed. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was dissolved with 100 mL of ethyl acetate. The resulting mixture was washed 2 times with 100 mL of NaCl(aq.). The final product was purified by recrystallization from MeOH/H2O in the ratio 2:3. This resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid. Into a 500 mL round bottom flask was placed To the mixture was added CH3COOAg (31.6 g, 189.22 mmol) to react A filtration The filtrate was concentrated by evaporation under vacuum a rotary evaporator The resulting solution was dissolved with 100 mL of ethyl acetate The resulting mixture was washed 2 times with 100 mL of NaCl(aq.) The final product was purified by recrystallization from MeOH/H2O in the ratio 2:3 This resulted in 8.5 g (41%) of 1H-indol-3-yl acetate as a dark purple solid

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

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

Procedure: In accordance with the procedures described previously, 10 mg of eel cholinesterase (Code ECH, Worthington Biochemical Company, approximately 100 units/mg) is dissolved in 30 ml of the 0.5 M, pH 8.0, "TRITON X-100"-containing 1,4-bis(3-sulfopropyl) piperazine buffer solution described previously. Then 30 microliters of the resulting buffered eel cholinesterase solution (i.e. 1.0 unit of the enzyme) were impregnated into 12.7 mm discs of DE81 (diethylaminoethyl ion exchange paper, 3.5 microequivalents per cm2) paper (DEAE) discs, allowed to air-dry for 3 hours at room temperature, placed in uncapped glass vials and allowed to dry for 12 hours at 0.01 mm Hg, at 25° C. in a vacuum desiccator. Indoxyl acetate discs were prepared from the following solution and 9.0 cm Whatman No. 1 filter paper circles. to air-dry for 3 hours at room temperature to dry for 12 hours at 0.01 mm Hg, at 25° C. in a vacuum desiccator 1 filter paper circles

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

Procedure: In accordance with the procedures described previously, 10 mg of eel cholinesterase (Code ECH, Worthington Biochemical Company, approximately 100 units/mg) is dissolved in 30 ml of the 0.5 M, pH 8.0, "TRITON X-100"-containing 1,4-bis(3-sulfopropyl) piperazine buffer solution described previously. Then 30 microliters of the resulting buffered eel cholinesterase solution (i.e. 1.0 unit of the enzyme) were impregnated into 12.7 mm discs of DE81 (diethylaminoethyl ion exchange paper, 3.5 microequivalents per cm2) paper (DEAE) discs, allowed to air-dry for 3 hours at room temperature, placed in uncapped glass vials and allowed to dry for 12 hours at 0.01 mm Hg, at 25° C. in a vacuum desiccator. Indoxyl acetate discs were prepared from the following solution and 9.0 cm Whatman No. 1 filter paper circles. to air-dry for 3 hours at room temperature to dry for 12 hours at 0.01 mm Hg, at 25° C. in a vacuum desiccator 1 filter paper circles

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

Procedure: Argon gas was blown into a suspension of indoxyl acetate (1.75 g, 10 mmol) and isatin (1.47 g, 10 mmol) in anhydrous methanol (20 mL) for 5 minutes. Sodium carbonate (2.12 g, 20 mmol) was added to the reaction liquid and stirred at room temperature for 18 hours. The reaction liquid was then poured into water (1 L). The precipitated crude crystals were collected by suction filtration. The resulting crude crystals were recrystallized from 1,4-dioxane/hexane to give purple needle-shaped crystals of indirubin (1.81 g, 69%). The reaction liquid The precipitated crude crystals were collected by suction filtration The resulting crude crystals were recrystallized from 1,4-dioxane/hexane