1-(2-IODOPHENYL)UREA

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a degassed solution of 1-(2-iodophenyl)urea (2.62 g, 10 mmol, 1 eq), ethynyltrimethyl silane (4.16 mL, 3 eq), and triethylamine (5.58 mL, 4 eq) in anhydrous DMF (15 mL) was added bis(triphenylphosphine)palladium(II) dichloride (702 mg, 0.1 eq) and copper(I) iodide (190.4 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 30 minutes, it was partitioned between aqueous ammonium chloride and ethyl acetate. The organic layer was isolated, washed further with saturated sodium bicarbonate, brine, and lastly dried with sodium sulfate. The upper solution was decanted, concentrated, and the brown solid residue was treated with a small amount of DCM. The mixture was stirred at room temperature for 30 minute and filtered to obtain 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea as a white solid in 1.645 g. The filtrate was concentrated and the residue was subject to a gradient column chromatography (EtOAc-hex from 1:100 to 1:1) to render 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea with a second crop of 0.432 g in a total yield of 90%. it was partitioned between aqueous ammonium chloride and ethyl acetate The organic layer was isolated washed further with saturated sodium bicarbonate, brine lastly dried with sodium sulfate The upper solution was decanted concentrated the brown solid residue was treated with a small amount of DCM The mixture was stirred at room temperature for 30 minute filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a degassed solution of 1-(2-iodophenyl)urea (2.62 g, 10 mmol, 1 eq), ethynyltrimethyl silane (4.16 mL, 3 eq), and triethylamine (5.58 mL, 4 eq) in anhydrous DMF (15 mL) was added bis(triphenylphosphine)palladium(II) dichloride (702 mg, 0.1 eq) and copper(I) iodide (190.4 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 30 minutes, it was partitioned between aqueous ammonium chloride and ethyl acetate. The organic layer was isolated, washed further with saturated sodium bicarbonate, brine, and lastly dried with sodium sulfate. The upper solution was decanted, concentrated, and the brown solid residue was treated with a small amount of DCM. The mixture was stirred at room temperature for 30 minute and filtered to obtain 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea as a white solid in 1.645 g. The filtrate was concentrated and the residue was subject to a gradient column chromatography (EtOAc-hex from 1:100 to 1:1) to render 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea with a second crop of 0.432 g in a total yield of 90%. it was partitioned between aqueous ammonium chloride and ethyl acetate The organic layer was isolated washed further with saturated sodium bicarbonate, brine lastly dried with sodium sulfate The upper solution was decanted concentrated the brown solid residue was treated with a small amount of DCM The mixture was stirred at room temperature for 30 minute filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the nitrogen degassed solution of 1-(2-iodophenyl)urea (1.31 g, 5 mmol, 1 eq), 3-ethynylaniline (0.8 mL, 1.5 eq), triphenylphosphine (32.8 mg, 0.025 eq), and triethylamine (2.1 mL, 3 eq) in anhydrous DMF (12.5 mL) was added copper(I) iodide (190.4 mg, 0.2 eq) and bis(triphenylphosphine)palladium(II) dichloride (351 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 10 minutes, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the solid mixture was subject to a gradient column chromatography (EtOAc-Hex 1:2 to MeOH-EtOAc 1:9) to give 1-{2-[(3-aminophenyl)ethynyl]phenyl}urea as a brown solid in amount of 1.26 g. washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine lastly dried with anhydrous sodium sulfate The upper solution was decanted concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the nitrogen degassed solution of 1-(2-iodophenyl)urea (1.31 g, 5 mmol, 1 eq), 3-ethynylaniline (0.8 mL, 1.5 eq), triphenylphosphine (32.8 mg, 0.025 eq), and triethylamine (2.1 mL, 3 eq) in anhydrous DMF (12.5 mL) was added copper(I) iodide (190.4 mg, 0.2 eq) and bis(triphenylphosphine)palladium(II) dichloride (351 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 10 minutes, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the solid mixture was subject to a gradient column chromatography (EtOAc-Hex 1:2 to MeOH-EtOAc 1:9) to give 1-{2-[(3-aminophenyl)ethynyl]phenyl}urea as a brown solid in amount of 1.26 g. washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine lastly dried with anhydrous sodium sulfate The upper solution was decanted concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a degassed solution of 1-(2-iodophenyl)urea (2.62 g, 10 mmol, 1 eq), ethynyltrimethyl silane (4.16 mL, 3 eq), and triethylamine (5.58 mL, 4 eq) in anhydrous DMF (15 mL) was added bis(triphenylphosphine)palladium(II) dichloride (702 mg, 0.1 eq) and copper(I) iodide (190.4 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 30 minutes, it was partitioned between aqueous ammonium chloride and ethyl acetate. The organic layer was isolated, washed further with saturated sodium bicarbonate, brine, and lastly dried with sodium sulfate. The upper solution was decanted, concentrated, and the brown solid residue was treated with a small amount of DCM. The mixture was stirred at room temperature for 30 minute and filtered to obtain 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea as a white solid in 1.645 g. The filtrate was concentrated and the residue was subject to a gradient column chromatography (EtOAc-hex from 1:100 to 1:1) to render 1-{2-[(trimethylsilyl)ethynyl]phenyl}urea with a second crop of 0.432 g in a total yield of 90%. it was partitioned between aqueous ammonium chloride and ethyl acetate The organic layer was isolated washed further with saturated sodium bicarbonate, brine lastly dried with sodium sulfate The upper solution was decanted concentrated the brown solid residue was treated with a small amount of DCM The mixture was stirred at room temperature for 30 minute filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To the nitrogen degassed solution of 1-(2-iodophenyl)urea (1.31 g, 5 mmol, 1 eq), 3-ethynylaniline (0.8 mL, 1.5 eq), triphenylphosphine (32.8 mg, 0.025 eq), and triethylamine (2.1 mL, 3 eq) in anhydrous DMF (12.5 mL) was added copper(I) iodide (190.4 mg, 0.2 eq) and bis(triphenylphosphine)palladium(II) dichloride (351 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 10 minutes, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the solid mixture was subject to a gradient column chromatography (EtOAc-Hex 1:2 to MeOH-EtOAc 1:9) to give 1-{2-[(3-aminophenyl)ethynyl]phenyl}urea as a brown solid in amount of 1.26 g. washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine lastly dried with anhydrous sodium sulfate The upper solution was decanted concentrated