methyl 7-bromo-3-methoxynaphthalene-2-carboxylate

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

実験手順: The compound is prepared by the reaction of 7-bromo-3-methoxy-2-naphthoic acid methyl ester (2.2 g, 7.45 mmol, 1 eq) with 3-methoxyphenylboric acid (1.37 g, 8.95 mmol, 1.5 eq) according to method A. Purification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 66%, 1.58 g. Purification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent

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

実験手順: A solution of sodium hydroxide (1.6 g, 40 mmol) in water (30 mL) was added to a solution of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid methyl ester (5.9 g, 20 mmol) in ethanol (100 mL) and the resulting mixture was heated at reflux for 2 hours. The reaction mixture was then cooled and concentrated under reduced pressure. The residue was acidified until pH 3 ca. by addition of an aqueous solution of hydrochloric acid. The resulting mixture was extracted twice with dichloromethane and the combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 5.329 g of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid as a cream colored solid. the resulting mixture was heated at reflux for 2 hours The reaction mixture was then cooled concentrated under reduced pressure The residue was acidified until pH 3 ca. by addition of an aqueous solution of hydrochloric acid The resulting mixture was extracted twice with dichloromethane the combined organic extracts were dried over anhydrous sodium sulfate filtered evaporated under reduced pressure

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

実験手順: A mixture of 7-bromo-3-hydroxy-naphthalene-2-carboxylic acid (J. Med. Chem. 1990, 33(1), 171) (5.3 g, 19.85 mmol), potassium carbonate (13.7 g, 99.25 mmol) and dimethylsulfate (3.8 mL, 45.66 mmol) in acetone (50 mL) was heated at reflux for 3.5 hours. The reaction mixture was then filtered; the filtrate was treated with water (5 mL) and the resulting mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure; the residue was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 5.946 g of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid methyl ester without further purifications. was heated at reflux for 3.5 hours The reaction mixture was then filtered the filtrate was treated with water (5 mL) The reaction mixture was concentrated under reduced pressure the residue was dissolved in dichloromethane dried over anhydrous sodium sulfate filtered evaporated under reduced pressure

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

実験手順: The compound is prepared by the reaction of 7-bromo-3-methoxy-2-naphthoic acid methyl ester (2.2 g, 7.45 mmol, 1 eq) with 3-methoxyphenylboric acid (1.37 g, 8.95 mmol, 1.5 eq) according to method A. Purification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent yielded the desired compound in a yield of 66%, 1.58 g. Purification by column chromatography with a gradient of hexane/dichloromethane 1/1 to 3/7 and dichloromethane/methanol 95/5 as the eluent