反应详情

温度

50 °C

A mixture of 3-nitrophenol (457 mg, 3.29 mmol) (Aldrich) and potassium carbonate powder (498 mg, 3.60 mmol) in dry THF (10 mL) and DMF (5 mL) was stirred at 50° C. for 15 minutes before a solution of 3-bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (1.00 g, 2.99 mmol) (from Example 1 supra) in THF (8+2 mL) was added. The reaction was stirred at 50° C. for 3 hours and the resulting mixture was concentrated to remove most of the solvent. The residue was dissolved in EtOAc (200 mL), washed with water (2×25 mL) and brine (25 mL), dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 90/10) to give 4-chloro-3-(3-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 911 mg, 78%).

1. additionwas added
2. concentrationthe resulting mixture was concentrated
3. customto remove most of the solvent
4. dissolutionThe residue was dissolved in EtOAc (200 mL)
5. washwashed with water (2×25 mL) and brine (25 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude product was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 90/10)