1-(4-amino-3-iodophenyl)ethanone

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

Procedure: 1-(4-amino-3-iodophenyl)ethanone was prepared according to method D Step I with Iodine (2.82 g; 11.10 mmol) silver sulphate (3.46 g; 11.10 mmol) and 1-(4-aminophenyl)ethanone (1.50 g; 11.10 mmol) in ethanol (40 mL). The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.514 g (18%) of 1-(4-amino-3-iodophenyl)ethanone as a pale yellow solid. 1-(4-amino-3-iodophenyl)ethanone was prepared The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

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

Procedure: 1-(4-amino-3-iodophenyl)ethanone was prepared according to method D Step I with Iodine (2.82 g; 11.10 mmol) silver sulphate (3.46 g; 11.10 mmol) and 1-(4-aminophenyl)ethanone (1.50 g; 11.10 mmol) in ethanol (40 mL). The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.514 g (18%) of 1-(4-amino-3-iodophenyl)ethanone as a pale yellow solid. 1-(4-amino-3-iodophenyl)ethanone was prepared The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

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

Procedure: To a stirred suspension of CaCO3 (4.5 g, 45.27 mmol) in H2O (15 mL) was added a solution of 4-acetylaniline (4.1 g, 30.18 mmol) in MeOH (25 mL), followed by a solution of iodine monochloride (5.2 g, 31.88 mmol) in MeOH (20 mL) dropwise. The reaction was stirred at r.t. for 45 minutes, then diluted with Et2O (150 mL). The organic fraction was separated, washed with water (100 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (3.5 g, 44%) as a brown oil that was used without further purification. δH (DMSO-d6) 8.14 (1H, d, J 1.8 Hz), 7.70 (1H, dd, J 8.3 and 1.8 Hz), 6.75 (1H, d, J 8.3 Hz), 6.10 (2H, s), 2.41 (3H, s). LCMS (ES+) 261 (M)+, 283 (M+Na)+, RT 3.026 minutes (Method 5). The organic fraction was separated washed with water (100 mL) brine (100 mL), dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: To a stirred suspension of CaCO3 (4.5 g, 45.27 mmol) in H2O (15 mL) was added a solution of 4-acetylaniline (4.1 g, 30.18 mmol) in MeOH (25 mL), followed by a solution of iodine monochloride (5.2 g, 31.88 mmol) in MeOH (20 mL) dropwise. The reaction was stirred at r.t. for 45 minutes, then diluted with Et2O (150 mL). The organic fraction was separated, washed with water (100 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (3.5 g, 44%) as a brown oil that was used without further purification. δH (DMSO-d6) 8.14 (1H, d, J 1.8 Hz), 7.70 (1H, dd, J 8.3 and 1.8 Hz), 6.75 (1H, d, J 8.3 Hz), 6.10 (2H, s), 2.41 (3H, s). LCMS (ES+) 261 (M)+, 283 (M+Na)+, RT 3.026 minutes (Method 5). The organic fraction was separated washed with water (100 mL) brine (100 mL), dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: To a stirred suspension of CaCO3 (4.5 g, 45.27 mmol) in H2O (15 mL) was added a solution of 4-acetylaniline (4.1 g, 30.18 mmol) in MeOH (25 mL), followed by a solution of iodine monochloride (5.2 g, 31.88 mmol) in MeOH (20 mL) dropwise. The reaction was stirred at r.t. for 45 minutes, then diluted with Et2O (150 mL). The organic fraction was separated, washed with water (100 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (3.5 g, 44%) as a brown oil that was used without further purification. δH (DMSO-d6) 8.14 (1H, d, J 1.8 Hz), 7.70 (1H, dd, J 8.3 and 1.8 Hz), 6.75 (1H, d, J 8.3 Hz), 6.10 (2H, s), 2.41 (3H, s). LCMS (ES+) 261 (M)+, 283 (M+Na)+, RT 3.026 minutes (Method 4). The organic fraction was separated washed with water (100 mL) brine (100 mL), dried (Na2SO4) filtered concentrated in vacuo

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

Procedure: 1-(4-Amino-3-iodophenyl)ethanone (0.100 g; 0.383 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide 0.151 g; 0.383 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.016 g; 0.019 mmol), lithium chloride (0.016 mg; 0.383 mmol) and sodium carbonate (0.081 g; 0.766 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100° C. for 18 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.043 g (21%) of the title compound as a yellow oil. The solution was concentrated under reduced pressure diluted in ethyl acetate The organic layer was successively washed with brine, sodium thiosulfate dried concentrated under reduced pressure The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane)

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

Procedure: Iodine (2.82 g; 11.10 mmol) was added to a stirred mixture of silver sulphate (3.46 g; 11.10 mmol) and 1-(4-aminophenyl)ethanone (1.50 g; 11.10 mmol) in ethanol (40 mL). The reaction mixture was then stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulfate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.514 g (18%) of the title compound as a pale yellow solid. filtered over celite The volatiles were removed under reduced pressure the residue was partitioned between ethyl acetate The organic layer was washed with brine dried concentrated under reduced pressure The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

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

Procedure: 1-(4-amino-3-iodophenyl)ethanone was prepared according to method D Step I with Iodine (2.82 g; 11.10 mmol) silver sulphate (3.46 g; 11.10 mmol) and 1-(4-aminophenyl)ethanone (1.50 g; 11.10 mmol) in ethanol (40 mL). The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to yield 0.514 g (18%) of 1-(4-amino-3-iodophenyl)ethanone as a pale yellow solid. 1-(4-amino-3-iodophenyl)ethanone was prepared The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

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

Procedure: To a stirred suspension of CaCO3 (4.5 g, 45.27 mmol) in H2O (15 mL) was added a solution of 4-acetylaniline (4.1 g, 30.18 mmol) in MeOH (25 mL), followed by a solution of iodine monochloride (5.2 g, 31.88 mmol) in MeOH (20 mL) dropwise. The reaction was stirred at r.t. for 45 minutes, then diluted with Et2O (150 mL). The organic fraction was separated, washed with water (100 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (3.5 g, 44%) as a brown oil that was used without further purification. δH (DMSO-d6) 8.14 (1H, d, J 1.8 Hz), 7.70 (1H, dd, J 8.3 and 1.8 Hz), 6.75 (1H, d, J 8.3 Hz), 6.10 (2H, s), 2.41 (3H, s). LCMS (ES+) 261 (M)+, 283 (M+Na)+, RT 3.026 minutes (Method 5). The organic fraction was separated washed with water (100 mL) brine (100 mL), dried (Na2SO4) filtered concentrated in vacuo