6-bromo-7-methyl-1H-indole-2,3-dione

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: Chloral alcoholate (0.43 g, 1.05 eq) and Na2SO4 (2.84 g, 20 mmol) were dissolved in 10 mL water. 3-Bromo-2-methylaniline (0.33 g, 1.77 mmol)was added to the solution followed by 0.16 mL conc. HCl aqueous solution and NH2OH.HCl (0.38 g, 3.0 eq). The mixture was refluxed for 15 min and stirring was continued for additional 1 hr at RT. The precipitate was collected by filtration, washed with water and dried under vacuum. This precipitate was dissolved in 1 mL H2SO4 and the solution was heated (80° C.) for 15 min. After cooling down to RT, the mixture was poured into ice-water mixture and the precipitate was collected, washed with water and dried under vacuum to give the title compound (0.26 g, 61%). The mixture was refluxed for 15 min The precipitate was collected by filtration washed with water dried under vacuum This precipitate was dissolved in 1 mL H2SO4 After cooling down to RT the mixture was poured into ice-water mixture the precipitate was collected washed with water dried under vacuum

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: Chloral alcoholate (0.43 g, 1.05 eq) and Na2SO4(2.84 g, 20 mmol) were dissolved in 10 mL water. 3-Bromo-2-methylaniline (0.33 g, 1.77 mmol) was added to the solution followed by 0.16 mL conc. HCl aqueous solution and NH2OH.HCl (0.38 g, 3.0 eq). The mixture was refluxed for 15 min and stirring was continued for additional 1 hr at RT. The precipitate was collected by filtration, washed with water and dried under vacuum. This precipitate was dissolved in 1 mL H2SO4 and the solution was heated (80° C.) for 15 min. After cooling down to RT, the mixture was poured into ice-water mixture and the precipitate was collected, washed with water and dried under vacuum to give the title compound (0.26 g, 61%). The mixture was refluxed for 15 min The precipitate was collected by filtration washed with water dried under vacuum This precipitate was dissolved in 1 mL H2SO4 After cooling down to RT the mixture was poured into ice-water mixture the precipitate was collected washed with water dried under vacuum

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

Procedure: H2O2 (37%, 9.5 mL, 0.075 mol) in H2O (83 mL) is slowly added to a solution of 6-Bromo-7-methyl-1H-indole-2,3-dione (8.4 g, 0.035 mol) and NaOH (9.6 g, 0.24 mol) in H2O (185 mL) then stirred at room temperature for 1 h, After reaction, the mixture is filtered and the solid is dried under vacuum to give product. After reaction the mixture is filtered the solid is dried under vacuum to give product

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

Procedure: A mixture of N-(3-Bromo-2-methyl-phenyl)-2-hydroxyimino-acetamide (18.0 g, 0.07 mol), conc.H2SO4 (150 mL) is stirred at 80° C. for 1 h. After reaction, poured the reaction mixture to ice water (2 L) the mixture is filtered and the solid is dried under vacuum to give product. After reaction is filtered the solid is dried under vacuum to give product

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: Chloral alcoholate (0.43 g, 1.05 eq) and Na2SO4 (2.84 g, 20 mmol) were dissolved in 10 mL water. 3-Bromo-2-methylaniline (0.33 g, 1.77 mmol) was added to the solution followed by 0.16 mL conc. HCl aqueous solution and NH2OH.HCl (0.38 g, 3.0 eq). The mixture was refluxed for 15 min and stirring was continued for additional 1 hr at RT. The precipitate was collected by filtration, washed with water and dried under vacuum. This precipitate was dissolved in 1 mL H2SO4 and the solution was heated (80° C.) for 15 min. After cooling down to RT, the mixture was poured into ice-water mixture and the precipitate was collected, washed with water and dried under vacuum to give the title compound (0.26 g, 61%). The mixture was refluxed for 15 min The precipitate was collected by filtration washed with water dried under vacuum This precipitate was dissolved in 1 mL H2SO4 After cooling down to RT the mixture was poured into ice-water mixture the precipitate was collected washed with water dried under vacuum

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

Procedure: 6-Bromo-7-methyl-1H-indole-2,3-dione (100 mg, 0.38 mmol) and phenylboronic acid (53 mg, 1.1 eq) were dissolved in 10 mL DME. Pd(PPh3)4 (22 mg, 0.05 eq) were added followed by NaHCO3 (65 mg, 2.0 eq) dissolved in 10 mL water. The mixture was refluxed for 2.5 hr and the organic solvent was removed by evaporation. The mixture was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4 and purified by SiO2 chromatography to give the title compound (50 mg, 51%). The mixture was refluxed for 2.5 hr the organic solvent was removed by evaporation The mixture was extracted with ethyl acetate the combined organic layers were dried over Na2SO4 purified by SiO2 chromatography

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

Procedure: Chloral alcoholate (0.43 g, 1.05 eq) and Na2SO4 (2.84 g, 20 mmol) were dissolved in 10 mL water. 3-Bromo-2-methylaniline (0.33 g, 1.77 mmol) was added to the solution followed by 0.16 mL conc. HCl aqueous solution and NH2OH.HCl (0.38 g, 3.0 eq). The mixture was refluxed for 15 min and stirring was continued for additional 1 hr at RT. The precipitate was collected by filtration, washed with water and dried under vacuum. This precipitate was dissolved in 1 mL H2SO4 and the solution was heated (80° C.) for 15 min. After cooling down to RT, the mixture was poured into ice-water mixture and the precipitate was collected, washed with water and dried under vacuum to give the title compound (0.26 g, 61%). The mixture was refluxed for 15 min The precipitate was collected by filtration washed with water dried under vacuum This precipitate was dissolved in 1 mL H2SO4 After cooling down to RT the mixture was poured into ice-water mixture the precipitate was collected washed with water dried under vacuum