benzoyl bromide

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:

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

実験手順: To a solution of compound of example 223 (100 mg, 0.295 mmol) in dichloromethane (3 mL), pyridine (70.53 mg, 0.885 mmol) was added and stirred for 5 min followed by addition of benzoyl bromide (81.96 mg, 0.443 mmol). The reaction mixture was stirred for about 16 h. After completion of the reaction, the solvent was evaporated to obtain the title compound, which was directly used for the preparation of compound of example 305. The reaction mixture was stirred for about 16 h After completion of the reaction the solvent was evaporated

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

実験手順: 39.8 g (0.21 mol) of tin(II) chloride and 21.0 g (0.21 mol) of acetylacetone in 200 ml of diethyl ether were placed in a reactor. 38.8 g (0.21 mol) of benzoyl bromide were metered in over 15 min at room temperature, with stirring, a rise in temperature to the reflux point being recorded. After a postreaction time of 1 h at the reflux temperature, the mixture was cooled and the crystalline precipitate was separated off. 48 g (65% of theory) of 1-methylbut-1-en-3-onyltin bromide dichloride (BrCl2Sn--C(CH3)=CH--CO--CH3) were isolated. were metered in over 15 min at room temperature After a postreaction time of 1 h at the reflux temperature, the mixture was cooled the crystalline precipitate was separated off

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

実験手順: In the same manner as described in Example 1 but using 2.6 g (0.02 mole) of 5-fluorouracil, 10 ml of absolute pyridine and 7.4 g (0.04 mole) of benzoyl bromide, 1.6 g of 3-N-benzoyl-5-fluorouracil (yield, 34%) and 270 mg of 1,3-di-N-benzoyl-5-fluorouracil (yield, 4%) were obtained.

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

実験手順: 1H-pyrrolo[2,3-b]pyridine-N-oxide (154, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification. In a separate dry flask It was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine The organic layer was dried over sodium sulfate evaporated The crude material was taken directly to the next step without further purification

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

実験手順: 1H-pyrrolo[2,3-b]pyridine-N-oxide (154, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification. In a separate dry flask It was then washed with 3×30 ml, NaHCO3 (aq., satd.) and 1×30 mL brine The organic layer was dried over sodium sulfate evaporated The crude material was taken directly to the next step without further purification

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

実験手順: 1H-pyrrolo[2,3-b]pyridine-N-oxide (585, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification. In a separate dry flask It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine The organic layer was dried over sodium sulfate evaporated The crude material was taken directly to the next step without further purification

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

実験手順: 1H-pyrrolo[2,3-b]pyridine-N-oxide (585, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification. In a separate dry flask It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine The organic layer was dried over sodium sulfate evaporated The crude material was taken directly to the next step without further purification

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

実験手順: 1H-pyrrolo[2,3-b]pyridine-N-oxide (585, 500 mg, 3.72 mmol) was dissolved in 40 mL of dry benzene. In a separate dry flask, benzoyl bromide (2.5 equiv) and 1,1,1,3,3,3-hexamethyldisilazane (1.0 equiv) were combined in 20 mL of dry benzene. The bromide solution was added in 5 mL aliquots over 30 minutes to the reaction flask. The reaction was stirred at ambient temperature for two hours. It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine. The organic layer was dried over sodium sulfate and evaporated. The crude material was taken directly to the next step without further purification. In a separate dry flask It was then washed with 3×30 mL NaHCO3 (aq., satd.) and 1×30 mL brine The organic layer was dried over sodium sulfate evaporated The crude material was taken directly to the next step without further purification

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

実験手順: A mixture of 1 g of 5-{4-[6-hydroxy-4-(E)-hydroxyimino-2,5,7,8tetramethylchroman-2-ylmethoxy ]benzyl}-thiazolidine-2,4-dione (prepared as described in Example 13), 1.7 g of benzoyl bromide, 10 ml of pyridine and 5 ml of dimethylformamide was allowed to stand for 6 days at room temperature, after which it was heated for 8 hours at 60°-80° C. An aqueous solution of potassium carbonate and ethyl acetate were then added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography eluted with a 4:3 by volume mixture of hexane and ethyl acetate, to give the title compound, softening at 101°-107° C. after which it was heated for 8 hours at 60°-80° C The organic layer was separated dried over anhydrous sodium sulfate The solvent was distilled off the residue was purified by silica gel column chromatography eluted with a 4:3 by volume mixture of hexane and ethyl acetate