1-(2-amino-5-iodophenyl)ethanone

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 250 mL round-bottom flask, was placed a solution of 1-(2-amino-5-iodophenyl)ethanone (as prepared in the previous step, 6.5 g, 24.90 mmol, 1.00 equiv) in tetrahydrofuran (150 mL) and 1N HCl (49 mL, 2.00 equiv) and NaNO2 (2.3 g, 27.06 mmol, 1.10 equiv). The reaction mixture was stirred for 1 h at 0° C., and then was heated to reflux for 2 h. after cooled to room temperature, the solid were collected by filtration and washed with ice water. The title compound was obtained as a brown solid. Into a 250 mL round-bottom flask, was placed was heated to reflux for 2 h. after cooled to room temperature the solid were collected by filtration washed with ice water

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 250 mL round-bottom flask, was placed a solution of 1-(2-aminophenyl)ethanone (11 g, 81.48 mmol, 1.00 equiv) in 1N HCl (300 mL). This was followed by the addition of a solution of ICl (14.5 g, 89.51 mmol, 1.10 equiv) in 2N HCl (50 mL) dropwise with stirring at 0° C. The reaction mixture was stirred for 2 h at room temperature in a water/ice bath. The solid were collected by filtration and then washed with 200 mL of ethyl acetate: MeOH (10:1). The title compound was obtained as a brown solid. Into a 250 mL round-bottom flask, was placed The reaction mixture was stirred for 2 h at room temperature in a water/ice bath The solid were collected by filtration washed with 200 mL of ethyl acetate: MeOH (10:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 250 mL round-bottom flask, was placed a solution of 1-(2-amino-5-iodophenyl)ethanone (as prepared in the previous step, 6.5 g, 24.90 mmol, 1.00 equiv) in tetrahydrofuran (150 mL) and 1N HCl (49 mL, 2.00 equiv) and NaNO2 (2.3 g, 27.06 mmol, 1.10 equiv). The reaction mixture was stirred for 1 h at 0° C., and then was heated to reflux for 2 h. after cooled to room temperature, the solid were collected by filtration and washed with ice water. The title compound was obtained as a brown solid. Into a 250 mL round-bottom flask, was placed was heated to reflux for 2 h. after cooled to room temperature the solid were collected by filtration washed with ice water

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 250 mL round-bottom flask, was placed a solution of 1-(2-aminophenyl)ethanone (11 g, 81.48 mmol, 1.00 equiv) in 1N HCl (300 mL). This was followed by the addition of a solution of ICl (14.5 g, 89.51 mmol, 1.10 equiv) in 2N HCl (50 mL) dropwise with stirring at 0° C. The reaction mixture was stirred for 2 h at room temperature in a water/ice bath. The solid were collected by filtration and then washed with 200 mL of ethyl acetate: MeOH (10:1). The title compound was obtained as a brown solid. Into a 250 mL round-bottom flask, was placed The reaction mixture was stirred for 2 h at room temperature in a water/ice bath The solid were collected by filtration washed with 200 mL of ethyl acetate: MeOH (10:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A flask charged with 1-(2-aminophenyl)ethanone (405 mg) and DCM (20 mL) was cooled in an ice/water bath and NIS (675 mg) was added in three portions. The reaction was stirred at 0° C. The reaction mixture was diluted with 30 mL DCM, washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by preparative RP-HPLC, affording the title compound. MS (ESI+): m/z 262.06 (MH+). 1H NMR (400 MHz, CDCl3): δ 7.94 (s, 1H), 7.44 (d, J=8.8 Hz, 1H), 6.43 (d, J=8.8 Hz, 1H), 6.32 (br, 2H), 2.53 (s, 3H). was cooled in an ice/water bath washed with sat. aqueous NaHCO3 dried over Na2SO4 filtered concentrated under reduced pressure The crude material was purified by preparative RP-HPLC