2-bromo-1-(4-iodophenyl)ethanone

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 2.50 g (7.69 mmol) 2-bromo-1-(4-iodo-phenyl)-ethanone in 30 mL ACN are added 1.90 g (23.1 mmol) 4-methylimidazole and the mixture is stirred at rt for 48 h. After that time, the solvent is evaporated and the residue is taken up in EtOAc. The mixture is washed with water and brine (2×) and the organic layer is dried over magnesium sulphate. The solvent is evaporated and the residue is recrystallized from diethyl ether to yield the desired product. After that time, the solvent is evaporated The mixture is washed with water and brine (2×) the organic layer is dried over magnesium sulphate The solvent is evaporated the residue is recrystallized from diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of bromine (79.3 g, 508 mmol) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL). The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3×50 mL). The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M−Br)+264 (M−Br+NH4)+. concentrated under reduced pressure the residue was diluted with ethyl acetate (100 mL) washed with brine (3×50 mL) The organic layer was concentrated the residue was crystallized from ethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of bromine (79.3 g, 508 mmol) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL). The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3×50 mL). The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M−Br)+264 (M−Br+NH4)+. concentrated under reduced pressure the residue was diluted with ethyl acetate (100 mL) washed with brine (3×50 mL) The organic layer was concentrated the residue was crystallized from ethyl ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolving 27 g (83 mmol) of crude 2-bromo-4′-iodo acetophenone thus obtained and 8.0 g (85 mmol) of 2-aminopyridine into 200 milliliter of ethanol, adding 10 g of sodium hydrogen carbonate, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and ethanol, thereby obtaining 21 g of 2-(4-iodophenyl)-imidazo [1,2-a] pyridine (yield: 82%). thus obtained under heating for 6 hours After completion of the reaction, separation with filtration resultant crystals were washed with water and ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolving 27 g (83 mmol) of crude 2-bromo-4′-iodo acetophenone thus obtained and 8.0 g (85 mmol) of 2-aminopyridine into 200 milliliter of ethanol, adding 10 g of sodium hydrogen carbonate, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and ethanol, thereby obtaining 21 g of 2-(4-iodophenyl)-imidazo [1,2-a] pyridine (yield: 82%). thus obtained under heating for 6 hours After completion of the reaction, separation with filtration resultant crystals were washed with water and ethanol

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolving 20 g (81 mmol) of 4′-iodo acetophenone into 200 milliliter of acetic acid, and adding 12.8 g (81 mmol) of bromine while cooling with ice, stirred at the temperature of 15° C. for 3 hours. After the color of bromine disappeared, adding water and separating the precipitated solids by filtration, thereby obtained 27 g of crude 2-bromo-4′-iodo acetophenone. while cooling with ice separating the precipitated solids by filtration

反応条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolving 20 g (81 mmol) of 4′-iodo acetophenone into 200 milliliter of acetic acid, and adding 12.8 g (81 mmol) of bromine while cooling with ice, stirred at the temperature of 15° C. for 3 hours. After the color of bromine disappeared, adding water and separating the precipitated solids by filtration, thereby obtained 27 g of crude 2-bromo-4′-iodo acetophenone. while cooling with ice separating the precipitated solids by filtration

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL) was added the bromine (Aldrich, 79.3 g, 508 mmol, in 50 mL of acetic acid) and stirred at room temperature for 10 hours. It was concentrated under reduced pressure. The residue was then diluted with ethyl acetate (100 mL) and washed with brine (3×50 mL). The organic solution was concentrated. The title compound was obtained as yellow solid by recrystallization from diethyl ether (150 g, 91%). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 (d, J=8.5 Hz, 2 H) ppm; MS (DCl/NH3) m/z 246 (M−Br)+, 264 (M−Br+NH4)+. It was concentrated under reduced pressure The residue was then diluted with ethyl acetate (100 mL) washed with brine (3×50 mL) The organic solution was concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of bromine (79.3 g, 508 mmo) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL). The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3×50 mL). The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M—Br)+264 (M—Br+NH4)+. concentrated under reduced pressure the residue was diluted with ethyl acetate (100 mL) washed with brine (3×50 mL) The organic layer was concentrated the residue was crystallized from ethyl ether

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of crude 2-bromo-1-(4-iodophenyl)ethanone (18.2 g), 2-amino-3-picoline (1.1 equiv, 61.6 mmol), and sodium bicarbonate (1.3 equiv, 72.8 mmol) in isopropanol (160 mL) was heated at 80° C. for 16 h. After concentrating the reaction mixture in vacuo, water (100 mL) was added and the resultant tan slurry was filtered, rinsing with water (2×50 mL). The brown solid was recrystallized from hot isopropanol and further dried in vacuo to provide the title product as a brown solid (13.2 g, 71%). ESMS [M+H]+: 335.0. After concentrating the reaction mixture in vacuo, water (100 mL) was added the resultant tan slurry was filtered rinsing with water (2×50 mL) The brown solid was recrystallized from hot isopropanol further dried in vacuo