4-bromo-2-methylbenzenesulfonamide

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

Procedure: Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.2 g, Example 33), 4-bromo-2-methylbenzenesulfonic acid amide (1.7 g, Example 79a), ethanol (3 ml), 2M aqueous sodium carbonate (0.7 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 80° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a foam (0.13 g). Prepared After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane

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

Procedure: Prepared by the method of Example 69a) using 3-bromo-4-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (1.51 g). Prepared by the method of Example 69a)

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

Procedure: Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.2 g, Example 33), 4-bromo-2-methylbenzenesulfonic acid amide (1.7 g, Example 79a), ethanol (3 ml), 2M aqueous sodium carbonate (0.7 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 80° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a foam (0.13 g). Prepared After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane

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

Procedure: Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.2 g, Example 33), 4-bromo-2-methylbenzenesulfonic acid amide (1.7 g, Example 79a), ethanol (3 ml), 2M aqueous sodium carbonate (0.7 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 80° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a foam (0.13 g). Prepared After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane

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

Procedure: Prepared by the method of Example 69a) using 3-bromo-4-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (1.51 g). Prepared by the method of Example 69a)

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

Procedure: Prepared according to the method described in Example 12b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.2 g, Example 33), 4-bromo-2-methylbenzenesulfonic acid amide (1.7 g, Example 79a), ethanol (3 ml), 2M aqueous sodium carbonate (0.7 ml) and tetrakis(triphenylphosphine)palladium (0) (0.03 g) with heating at 80° C. for 3 hours. After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as a foam (0.13 g). Prepared After work-up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane

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

Procedure: Prepared by the method of Example 69a) using 3-bromo-4-methylaniline (2.60 g, Example 78a)), sodium nitrite (1.05 g), concentrated hydrochloric acid (20 ml), anhydrous magnesium chloride (2.6 g), acetic acid saturated with sulfur dioxide (50 ml) and copper (II) chloride (0.37 g). The normal work-up and subsequent treatment with ammonium hydroxide (50 ml) followed by the same work-up afforded the subtitle compound as a solid (1.51 g). Prepared by the method of Example 69a)