5-溴-3-甲酰基-1H-吲哚-2-甲酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).

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

实验步骤: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH

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

实验步骤: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).

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

实验步骤: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: In a 1 L round bottom flask 10.5 mL of phosphorus oxychloride was added to 15.5 g of N-methylformanilide at room temperature that resulted in a yellow solid after 15 min. At this time, 170 mL of 1,2-dichloroethane and 20.1 g of ethyl 5-bromoindole-2-carboxylate were added. The resulting suspension was heated under reflux for 4 hours and then concentrated to remove the organic solvent. 75 g of sodium acetate in 750 mL of water were added and the solid suspension was stirred for 30 min at room temperature, filtered and washed 3 times with water. The crude material was dried under vacuum for 1 hour and swished with 500 mL of EtOH to yield 21.2 g of the title compound as off-white solid. resulted in a yellow solid after 15 min The resulting suspension was heated under reflux for 4 hours concentrated to remove the organic solvent 75 g of sodium acetate in 750 mL of water were added filtered washed 3 times with water The crude material was dried under vacuum for 1 hour

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

实验步骤: In a 1 L round bottom flask 10.5 mL of phosphorus oxychloride was added to 15.5 g of N-methylformanilide at room temperature that resulted in a yellow solid after 15 min. At this time, 170 mL of 1,2-dichloroethane and 20.1 g of ethyl 5-bromoindole-2-carboxylate were added. The resulting suspension was heated under reflux for 4 hours and then concentrated to remove the organic solvent. 75 g of sodium acetate in 750 mL of water were added and the solid suspension was stirred for 30 min at room temperature, filtered and washed 3 times with water. The crude material was dried under vacuum for 1 hour and swished with 500 mL of EtOH to yield 21.2 g of the title compound as off-white solid. resulted in a yellow solid after 15 min The resulting suspension was heated under reflux for 4 hours concentrated to remove the organic solvent 75 g of sodium acetate in 750 mL of water were added filtered washed 3 times with water The crude material was dried under vacuum for 1 hour

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

实验步骤: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).

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

实验步骤: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH

反应条件: temp:0.00; pressure:0.00; stir: