5-Bromo-2-chlorobenzyl amine

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

Procedure: To a solution of 5-bromo-2-chlorobenzenemethanamine (i.e. the product of Synthesis Example 2, Step A) (1.3 g, 5.5 mmol) in dichloromethane (25 mL) at 0° C. was added carbonyl diimidazole (1.4 g, 8.6 mmol). The reaction mixture was stirred at room temperature for 1 h. Then the reaction mixture was cooled to 0° C., a solution of methylamine in THF (2 M, 3.0 mL, 6.0 mmol) was added, and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was filtered, and the solid residue was washed with pentane to provide the title product (1.0 g). Then the reaction mixture was cooled to 0° C. the reaction mixture was stirred at room temperature for 4 h The reaction mixture was filtered the solid residue was washed with pentane

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

Procedure: N-[(5-bromo-2-chlorophenyl)methyl]acetamide (i.e. the product of Step B) (0.58 g, 2.2 mmol) was reacted with 3-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazole (i.e. the product of Step A of Synthesis Example 1) (0.40 g, 2.0 mmol) using a procedure analogous to Step B of Synthesis Example 1 to provide the title product, a compound of the present invention, as a solid (0.09 g). analogous to Step B of Synthesis Example 1

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2-chlorobenzenemethanamine (i.e. the product of Step A) (600 mg, 2.72 mmol) in toluene (10 mL) at 0° C. was added acetic anhydride (0.55 mL, 5.45 mmol). The reaction mixture was stirred at 100° C. for 3 h. The reaction mixture was then extracted with ethyl acetate (3×), and the organic layers were combined, washed with water and brine and dried (Na2SO4). The solvent was evaporated to provide the title product (600 mg). The reaction mixture was then extracted with ethyl acetate (3×) washed with water and brine dried (Na2SO4) The solvent was evaporated

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of chlorotrimethylsilane (3.55 mL, 27.2 mmol) in acetonitrile (70 mL) was added sodium iodide (3.91 g, 27.2 mmol), and the reaction mixture was stirred at −20° C. for 1 h. Then methyl N-[(5-bromo-2-chlorophenyl)methyl]carbamate (3 g, 7.7 mmol; prepared according to U.S. Pat. No. 6,313,071) was added, and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then basified with 1 N aqueous sodium hydroxide solution and extracted with ethyl acetate (3×). The organic layers were combined, washed with water and brine and then dried (Na2SO4). The solvent was evaporated to provide the title product (1.4 g). prepared 6,313,071) was added the reaction mixture was stirred at room temperature for 16 h extracted with ethyl acetate (3×) washed with water and brine dried (Na2SO4) The solvent was evaporated