乙基 7-溴-5-氟-1-苯并呋喃-2-羧酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzylpiperazine (1.3 mL, 8.4 mmol), BINAP (0.43 g, 0.69 mmol), Pd2 dba3 (0.32 g, 0.35 mmol), cesium carbonate (3.25 g, 9.76 mmol) were added to a degassed solution of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 6.97 mmol) in toluene (50 mL). The mixture was heated at reflux over night. After cooling, the mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3). Yield: 1.6 g (60%). The mixture was heated at reflux over night After cooling the mixture was filtered through a pad of celite washed with dichloromethane The filtrate was concentrated under reduced pressure The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzylpiperazine (1.3 mL, 8.4 mmol), BINAP (0.43 g, 0.69 mmol), Pd2 dba3 (0.32 g, 0.35 mmol), cesium carbonate (3.25 g, 9.76 mmol) were added to a degassed solution of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 6.97 mmol) in toluene (50 mL). The mixture was heated at reflux over night. After cooling, the mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3). Yield: 1.6 g (60%). The mixture was heated at reflux over night After cooling the mixture was filtered through a pad of celite washed with dichloromethane The filtrate was concentrated under reduced pressure The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzylpiperazine (1.3 mL, 8.4 mmol), BINAP (0.43 g, 0.69 mmol), Pd2 dba3 (0.32 g, 0.35 mmol), cesium carbonate (3.25 g, 9.76 mmol) were added to a degassed solution of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 6.97 mmol) in toluene (50 mL). The mixture was heated at reflux over night. After cooling, the mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3). Yield: 1.6 g (60%). The mixture was heated at reflux over night After cooling the mixture was filtered through a pad of celite washed with dichloromethane The filtrate was concentrated under reduced pressure The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzylpiperazine (1.3 mL, 8.4 mmol), BINAP (0.43 g, 0.69 mmol), Pd2 dba3 (0.32 g, 0.35 mmol), cesium carbonate (3.25 g, 9.76 mmol) were added to a degassed solution of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 6.97 mmol) in toluene (50 mL). The mixture was heated at reflux over night. After cooling, the mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3). Yield: 1.6 g (60%). The mixture was heated at reflux over night After cooling the mixture was filtered through a pad of celite washed with dichloromethane The filtrate was concentrated under reduced pressure The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzylpiperazine (1.3 mL, 8.4 mmol), BINAP (0.43 g, 0.69 mmol), Pd2 dba3 (0.32 g, 0.35 mmol), cesium carbonate (3.25 g, 9.76 mmol) were added to a degassed solution of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid ethyl ester (2.0 g, 6.97 mmol) in toluene (50 mL). The mixture was heated at reflux over night. After cooling, the mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3). Yield: 1.6 g (60%). The mixture was heated at reflux over night After cooling the mixture was filtered through a pad of celite washed with dichloromethane The filtrate was concentrated under reduced pressure The product was purified by flash chromatography (SiO2; hexane/EtOAc, 7/3)

反应条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product. cooled to rt quenched with water (20 mL) extracted twice with ethyl acetate The combined organic extracts were washed with brine dried (Na2SO4) filtered concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)