2-amino-4-ethylsulfonylphenol

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

Procedure: 100 mmol 1-amino-5-ethylsulfonyl-2-hydroxybenzene were dissolved in 200 ml of ethanol and 150 ml of carbon disulfide. 120 mmol of potassium hydroxide was added and the mixture refluxed over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate and dried. Evaporation gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. the mixture refluxed over night The solvent was evaporated the residue treated with 1 M hydrochloric acid extracted with ethyl acetate dried Evaporation gave the crude product which was recrystallized from ethyl acetate

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

Procedure: Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%). After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane

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

Procedure: Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%). After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane

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

Procedure: Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%). After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane

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

Procedure: 100 mmol 1-amino-5-ethylsulfonyl-2-hydroxybenzene were dissolved in 200 ml of ethanol and 150 ml of carbon disulfide. 120 mmol of potassium hydroxide was added and the mixture refluxed over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate and dried. Evaporation gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. the mixture refluxed over night The solvent was evaporated the residue treated with 1 M hydrochloric acid extracted with ethyl acetate dried Evaporation gave the crude product which was recrystallized from ethyl acetate

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

Procedure: 100 mmol 1-amino-5-ethylsulfonyl-2-hydroxybenzene were dissolved in 200 ml of ethanol and 150 ml of carbon disulfide. 120 mmol of potassium hydroxide was added and the mixture refluxed over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate and dried. Evaporation gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. the mixture refluxed over night The solvent was evaporated the residue treated with 1 M hydrochloric acid extracted with ethyl acetate dried Evaporation gave the crude product which was recrystallized from ethyl acetate

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

Procedure: To a solution of 1-amino-5-ethylsulfonyl-2-hydroxybenzene (20.13 g, 100.0 mmol, 1.0 equiv) in ethanol (200 mL) were added carbon disulfide (190.0 g, 150 mL, 2494 mmol, 25.0 equiv) and potassium hydroxide (6.73 g, 120 mmol, 1.2 equiv) and the reaction mixture heated to reflux over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate (3×150 mL) and the combined organic fractions dried over MgSO4. Evaporation of the organic solvent gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. MS (ISN): 242.4 [M−H]−. the reaction mixture heated to reflux over night The solvent was evaporated the residue treated with 1 M hydrochloric acid extracted with ethyl acetate (3×150 mL) the combined organic fractions dried over MgSO4 Evaporation of the organic solvent gave the crude product which was recrystallized from ethyl acetate

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-amino-4-(ethylsulfonyl)phenol (452.7 mg, 2.25 mmol) in ethanol (17 mL) was added 5-methyl-2-thiophenecarboxaldehyde (242 μL, 2.25 mmol). The mixture was heated at 70° C. for 70 min. After cooling, a small amount of precipitate was formed. After filtration and evaporation of the filtrate, the resulting product was dissolved in acetonitrile (9.8 mL) and lead tetraacetate (887 mg, 2 mmol) was added. The resulting mixture was heated at 100° C. for 5 min. After cooling, the reaction mixture was filtered off, and the filtrate evaporated in vacuo. The resulting mixture was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v, and then purified by reverse phase HPLC to afford 2.2 mg (0.3%) of the title product (LCMS RT=6.41 min, MH+ 308.1) After cooling a small amount of precipitate was formed After filtration and evaporation of the filtrate the resulting product was dissolved in acetonitrile (9.8 mL) The resulting mixture was heated at 100° C. for 5 min After cooling the reaction mixture was filtered off the filtrate evaporated in vacuo The resulting mixture was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v purified by reverse phase HPLC

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 2-amino-4-(ethylsulfonyl)phenol (452.7 mg, 2.25 mmol) in ethanol (17 mL) was added 5-methyl-2-thiophenecarboxaldehyde (242 μL, 2.25 mmol). The mixture was heated at 70° C. for 70 min. After cooling, a small amount of precipitate was formed. After filtration and evaporation of the filtrate, the resulting product was dissolved in acetonitrile (9.8 mL) and lead tetraacetate (887 mg, 2 mmol) was added. The resulting mixture was heated at 100° C. for 5 min. After cooling, the reaction mixture was filtered off, and the filtrate evaporated in vacuo. The resulting mixture was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v, and then purified by reverse phase HPLC to afford 2.2 mg (0.3%) of the title product (LCMS RT=6.41 min, MH+ 308.1) After cooling a small amount of precipitate was formed After filtration and evaporation of the filtrate the resulting product was dissolved in acetonitrile (9.8 mL) The resulting mixture was heated at 100° C. for 5 min After cooling the reaction mixture was filtered off the filtrate evaporated in vacuo The resulting mixture was purified by column chromatography eluting with ethyl acetate/hexanes 20:80 v/v purified by reverse phase HPLC

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

Procedure: Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%). After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane

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

Procedure: 100 mmol 1-amino-5-ethylsulfonyl-2-hydroxybenzene were dissolved in 200 ml of ethanol and 150 ml of carbon disulfide. 120 mmol of potassium hydroxide was added and the mixture refluxed over night. The solvent was evaporated, the residue treated with 1 M hydrochloric acid, extracted with ethyl acetate and dried. Evaporation gave the crude product which was recrystallized from ethyl acetate to yield the title compound as yellowish solid. the mixture refluxed over night The solvent was evaporated the residue treated with 1 M hydrochloric acid extracted with ethyl acetate dried Evaporation gave the crude product which was recrystallized from ethyl acetate

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

Procedure: Commercially available 4-ethylsulfonyl-2-aminophenol (4.02 g, 20 mmol) was dissolved in DMF (30 mL) and mixed with cesium carbonate (6.5 g, 20 mmol). The reaction mixture was cooled to 0° C. and bromoacetyl bromide (4.0 g, 20 mmol) in DMF (5 mL) was added dropwise. The reaction was stirred overnight at room temperature. After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane to give the product as an orange solid, 1.7 g (35%). After aqueous work up, the product was purified by silica gel chromatography with methanol/dichloromethane