2-bromo-4-chloro-5-methoxyaniline

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of Example 18A (1.0 equivalents), cyclopropyl boronic acid (1.1 equivalents), tricyclohexylphosphine (0.05 equivalents), palladium acetate (0.025 equivalents) and K3PO4 (2 equivalents) in a 20:1 volume ratio of toluene and water was sparged with nitrogen for 15 minutes. The reaction mixture was then heated to 100° C. for 12 hours, cooled, diluted with water, stirred for 1 hour and filtered through a diatomaceous earth pad, and the pad was rinsed with toluene. The filtrate was mixed and the layers were separated. The organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated to an oil that was used without further purification. cooled filtered through a diatomaceous earth pad the pad was rinsed with toluene The filtrate was mixed the layers were separated The organic layer was washed with water and saturated brine dried (Na2SO4) filtered concentrated to an oil that was used without further purification

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

Procedure: A mixture of Example 18A (1.0 equivalents), cyclopropyl boronic acid (1.1 equivalents), tricyclohexylphosphine (0.05 equivalents), palladium acetate (0.025 equivalents) and K3PO4 (2 equivalents) in a 20:1 volume ratio of toluene and water was sparged with nitrogen for 15 minutes. The reaction mixture was then heated to 100° C. for 12 hours, cooled, diluted with water, stirred for 1 hour and filtered through a diatomaceous earth pad, and the pad was rinsed with toluene. The filtrate was mixed and the layers were separated. The organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated to an oil that was used without further purification. cooled filtered through a diatomaceous earth pad the pad was rinsed with toluene The filtrate was mixed the layers were separated The organic layer was washed with water and saturated brine dried (Na2SO4) filtered concentrated to an oil that was used without further purification

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

Procedure: A solution of 4-chloro-3-methoxyaniline (1.0 equivalent) dissolved in CH2Cl2 (15 volumes) at 5° C. was treated portion wise with N-bromosuccinimide (1.03 equivalents), warmed to 20° C. and mixed for 5 minutes. A 5% aqueous Na2SO3 solution (10 volumes) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated. The resulting solid was triturated with a minimal volume of heptane and the solid was collected by filtration and dried to constant mass (80% yield). mixed for 5 minutes The layers were separated the organic layer was washed with water and saturated brine dried (Na2SO4) filtered concentrated The resulting solid was triturated with a minimal volume of heptane the solid was collected by filtration dried to constant mass (80% yield)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of Example 18A (1.0 equivalents), cyclopropyl boronic acid (1.1 equivalents), tricyclohexylphosphine (0.05 equivalents), palladium acetate (0.025 equivalents) and K3PO4 (2 equivalents) in a 20:1 volume ratio of toluene and water was sparged with nitrogen for 15 minutes. The reaction mixture was then heated to 100° C. for 12 hours, cooled, diluted with water, stirred for 1 hour and filtered through a diatomaceous earth pad, and the pad was rinsed with toluene. The filtrate was mixed and the layers were separated. The organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated to an oil that was used without further purification. cooled filtered through a diatomaceous earth pad the pad was rinsed with toluene The filtrate was mixed the layers were separated The organic layer was washed with water and saturated brine dried (Na2SO4) filtered concentrated to an oil that was used without further purification

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

Procedure: A solution of 4-chloro-3-methoxyaniline (1.0 equivalent) dissolved in CH2Cl2 (15 volumes) at 5° C. was treated portion wise with N-bromosuccinimide (1.03 equivalents), warmed to 20° C. and mixed for 5 minutes. A 5% aqueous Na2SO3 solution (10 volumes) was added and the mixture was stirred for 10 minutes. The layers were separated and the organic layer was washed with water and saturated brine, dried (Na2SO4), filtered and concentrated. The resulting solid was triturated with a minimal volume of heptane and the solid was collected by filtration and dried to constant mass (80% yield). mixed for 5 minutes The layers were separated the organic layer was washed with water and saturated brine dried (Na2SO4) filtered concentrated The resulting solid was triturated with a minimal volume of heptane the solid was collected by filtration dried to constant mass (80% yield)