3-bromo-2-methylbenzenesulfonyl chloride

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product

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

Procedure: Into a flask, 3-(5-fluoro-1H-indol-3-yl)-propionic acid methyl ester (3, 530.000 mg, 2.39572E-3 mol), 3-bromo-2-methyl-benzene sulfonyl chloride (4, 710.33 mg, 0.0026353 mol), 62.35 mL methylene chloride, 17 mL 50% KOH and a catalytic amount of tetra-n-butyl ammonium hydrogen sulfate were combined and stirred at room temperature for 48 hours. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4 and filtered. The organic layer was concentrated at reduced pressure to afford a tannish solid. Purification by flash chromatography using a gradient of 0-25% ethyl acetate in hexanes over 35 minutes yielded the desired compound (5, 650 mg, 59.72%). 1H NMR consistent with desired compound. MS(ESI) [M+H+]+==454.0, 456.0. The organic layer was washed with saturated sodium bicarbonate dried over MgSO4 filtered The organic layer was concentrated at reduced pressure to afford a tannish solid Purification by flash chromatography over 35 minutes

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product

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

Procedure: Into a flask, 3-(5-fluoro-1H-indol-3-yl)-propionic acid methyl ester (3, 530.000 mg, 2.39572E-3 mol), 3-bromo-2-methyl-benzene sulfonyl chloride (4, 710.33 mg, 0.0026353 mol), 62.35 mL methylene chloride, 17 mL 50% KOH and a catalytic amount of tetra-n-butyl ammonium hydrogen sulfate were combined and stirred at room temperature for 48 hours. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4 and filtered. The organic layer was concentrated at reduced pressure to afford a tannish solid. Purification by flash chromatography using a gradient of 0-25% ethyl acetate in hexanes over 35 minutes yielded the desired compound (5, 650 mg, 59.72%). 1H NMR consistent with desired compound. MS(ESI) [M+H+]+==454.0, 456.0. The organic layer was washed with saturated sodium bicarbonate dried over MgSO4 filtered The organic layer was concentrated at reduced pressure to afford a tannish solid Purification by flash chromatography over 35 minutes

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

Procedure: 3-Bromo-2-methylbenzene-1-sulfonyl chloride (300 mg) and 1-adamantanamine (185 mg) were dissolved in dichloromethane (4 mL). Diisopropylethylamine (432 mg) was added, and the solution was stirred at room temperature for 16 hours. The solution was diluted with 70% ethyl acetate (hexanes), washed three times with 1 M aqueous HCl, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed to yield the product. washed three times with 1 M aqueous HCl washed with brine dried over anhydrous sodium sulfate After filtration the solvent was removed to yield the product