6-bromo-3H-imidazo[1,2-a]pyridin-2-one

反応条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1.4 g of 6-bromo-3H-imidazo[1,2-a]pyridin-2-one in 5 ml of POCl3 is heated at 105° C. for 2 hours and then cooled to ambient temperature and concentrated under reduced pressure. The residue is taken up between water and dichloromethane and a 30% aqueous solution of NH4OH is added until a basic pH is obtained. The organic phase is then separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue is then purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 760 mg of compound are obtained. cooled to ambient temperature concentrated under reduced pressure a 30% aqueous solution of NH4OH is added until a basic pH is obtained The organic phase is then separated dried over magnesium sulphate concentrated under reduced pressure The residue is then purified by silica gel chromatography, elution

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

実験手順: 3.0 g of 5-bromopyridin-2-ylamine in 5.8 ml of ethyl 2-bromoacetate are placed in a round-bottomed flask and stirred at ambient temperature for 48 h. A precipitate forms, and is recovered by filtration, washed with diethyl ether and oven-dried under reduced pressure. The solid is then taken up in 50 ml of ethanol, and 2.18 g of sodium hydrogencarbonate are added thereto. The reaction mixture is heated at the reflux of the solvent for 5 h, cooled to ambient temperature, and then concentrated under reduced pressure. The residue obtained is taken up between water and dichloromethane and the organic phase is separated, dried and concentrated under reduced pressure. 1.46 g of compound, used as it is in the subsequent stages, are obtained. A precipitate forms, and is recovered by filtration washed with diethyl ether oven-dried under reduced pressure 2.18 g of sodium hydrogencarbonate are added The reaction mixture is heated at the reflux of the solvent for 5 h cooled to ambient temperature concentrated under reduced pressure The residue obtained the organic phase is separated dried concentrated under reduced pressure are obtained

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

実験手順: To a solution of 2-Amino-5-bromo-1-ethoxycarbonylmethyl-pyridinium; bromide (2.86 g, 8.4 mmol) in methanol (30 mL) was added sodium methoxide (25 wt %, 2.5 mL, 10.1 mmol). The reaction mixture was stirred at room temperature overnight under argon. The reaction mixture was diluted with water and then extracted three times with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, evaporated to yield a tan solid. The crude material was purified by column chromatography eluting with 3, 5, and 10% methanol/dichloromethane. The product was obtained as a brown solid (56 mg, 3%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.67 (dd, J=1.6, 9.5 Hz, 1H), 7.07 (d, J=9.5 Hz, 1H), 4.52 (s, 2H); MS (m/e): 215 (MH+); HRMS: calc'd MH+ for C7H5BrN2O 212.9672. Found 212.9664. extracted three times with ethyl acetate The organic extracts were washed with brine dried over magnesium sulfate filtered evaporated to yield a tan solid The crude material was purified by column chromatography eluting with 3, 5, and 10% methanol/dichloromethane

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

実験手順: To a solution of 2-Amino-5-bromo-1-ethoxycarbonylmethyl-pyridinium; bromide (2.86 g, 8.4 mmol) in methanol (30 mL) was added sodium methoxide (25 wt %, 2.5 mL, 10.1 mmol). The reaction mixture was stirred at room temperature overnight under argon. The reaction mixture was diluted with water and then extracted three times with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, evaporated to yield a tan solid. The crude material was purified by column chromatography eluting with 3, 5, and 10% methanol/dichloromethane. The product was obtained as a brown solid (56 mg, 3%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.67 (dd, J=1.6, 9.5 Hz, 1H), 7.07 (d, J=9.5 Hz, 1H), 4.52 (s, 2H); MS (m/e): 215 (MH+); HRMS: calc'd MH+ for C7H5BrN2O 212.9672; found 212.9664. extracted three times with ethyl acetate The organic extracts were washed with brine dried over magnesium sulfate filtered evaporated to yield a tan solid The crude material was purified by column chromatography eluting with 3, 5, and 10% methanol/dichloromethane