Hydrochloric Acid → HCID 66743701, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-3-(ethylamino)thiophene-2-carboxylate (2.46 g, 9.31 mmol) in MeOH (30 mL) was added a solution of sodium hydroxide (1.12 g, 27.9 mmol) in water (15 mL). After stirring at 60° C. for 4 h, 6 M aqueous HCl (2.9 mL) was added to the mixture to adjust the pH to 10. After removal of the solvent at reduced pressure, the residue was diluted with DMF (70 mL). Then, triethylamine (25.8 mL, 186 mmol) and ammonium chloride (10.0 g, 186 mmol) were added. After stirring at room temperature for 10 min, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (10.7 g, 55.9 mmol) and 1-hydroxybenzotriazole (7.55 g, 55.9 mmol) were added to the mixture and the stirring was continued for 17 h. Then, water and EtOAc were added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 70:30 hexane/EtOAc) to give the title compound (0.97 g, 42%) as a pale green solid:

Provenance & Evidence