2-(3-bromophenoxy)acetamide

Conditions: temp:90.01; 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 (0.150 g, Example 33), 2-(3-bromophenoxy)acetamide (0.230 g), 2M aqueous sodium carbonate (0.50 ml) and tetrakis(triphenylphosphine)palladium(0) (0.025 g) in ethanol (3 ml). The reaction mixture was heated at 90° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure, taken up in ethanol and concentrated again (twice). The residue was triturated with acetone and then filtered through silica gel. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane, filtered and purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised from boiling ethyl acetate:isohexane (1:1) to give the title compound as a solid (0.138 g). Prepared After cooling the solution was concentrated under reduced pressure concentrated again (twice) The residue was triturated with acetone filtered through silica gel The filtrate was concentrated under reduced pressure dissolved in dichloromethane filtered purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised

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

Procedure: A mixture of 2-chloroacetamide (5.6 g), 3-bromophenol (10 g), potassium carbonate (8.3 g) and potassium iodide (1 g) in acetonitrile was stirred at room temperature for 72 hours. The resulting mixture was filtered, and the solids washed with ethyl acetate, and then water. The dried solids were recrystallised from boiling ethanol: water(8:2) to give the sub-title compound as a solid (13.8 g). The resulting mixture was filtered the solids washed with ethyl acetate The dried solids were recrystallised

Conditions: temp:90.01; 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 (0.150 g, Example 33), 2-(3-bromophenoxy)acetamide (0.230 g), 2M aqueous sodium carbonate (0.50 ml) and tetrakis(triphenylphosphine)palladium(0) (0.025 g) in ethanol (3 ml). The reaction mixture was heated at 90° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure, taken up in ethanol and concentrated again (twice). The residue was triturated with acetone and then filtered through silica gel. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane, filtered and purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised from boiling ethyl acetate:isohexane (1:1) to give the title compound as a solid (0.138 g). Prepared After cooling the solution was concentrated under reduced pressure concentrated again (twice) The residue was triturated with acetone filtered through silica gel The filtrate was concentrated under reduced pressure dissolved in dichloromethane filtered purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised

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

Procedure: A mixture of 2-chloroacetamide (5.6 g), 3-bromophenol (10 g), potassium carbonate (8.3 g) and potassium iodide (1 g) in acetonitrile was stirred at room temperature for 72 hours. The resulting mixture was filtered, and the solids washed with ethyl acetate, and then water. The dried solids were recrystallised from boiling ethanol: water(8:2) to give the sub-title compound as a solid (13.8 g). The resulting mixture was filtered the solids washed with ethyl acetate The dried solids were recrystallised

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

Procedure: A mixture of 2-chloroacetamide (5.6 g), 3-bromophenol (10 g), potassium carbonate (8.3 g) and potassium iodide (1 g) in acetonitrile was stirred at room temperature for 72 hours. The resulting mixture was filtered, and the solids washed with ethyl acetate, and then water. The dried solids were recrystallised from boiling ethanol: water(8:2) to give the sub-title compound as a solid (13.8 g). The resulting mixture was filtered the solids washed with ethyl acetate The dried solids were recrystallised

Conditions: temp:90.01; 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 (0.150 g, Example 33), 2-(3-bromophenoxy)acetamide (0.230 g), 2M aqueous sodium carbonate (0.50 ml) and tetrakis(triphenylphosphine)palladium(0) (0.025 g) in ethanol (3 ml). The reaction mixture was heated at 90° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure, taken up in ethanol and concentrated again (twice). The residue was triturated with acetone and then filtered through silica gel. The filtrate was concentrated under reduced pressure, dissolved in dichloromethane, filtered and purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised from boiling ethyl acetate:isohexane (1:1) to give the title compound as a solid (0.138 g). Prepared After cooling the solution was concentrated under reduced pressure concentrated again (twice) The residue was triturated with acetone filtered through silica gel The filtrate was concentrated under reduced pressure dissolved in dichloromethane filtered purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a colourless solid, which was recrystallised

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

Procedure: A mixture of 2-chloroacetamide (5.6 g), 3-bromophenol (10 g), potassium carbonate (8.3 g) and potassium iodide (1 g) in acetonitrile was stirred at room temperature for 72 hours. The resulting mixture was filtered, and the solids washed with ethyl acetate, and then water. The dried solids were recrystallised from boiling ethanol: water(8:2) to give the sub-title compound as a solid (13.8 g). The resulting mixture was filtered the solids washed with ethyl acetate The dried solids were recrystallised