Hydrochloric Acid → HCID 66744013, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-amino-5-bromothiophene-2-carboxylate (1.2 g, 5.08 mmol) in MeOH (15 mL) was added sodium hydroxide (0.61 g, 15.2 mmol) and water (5 mL). After stirring at 60° C. for 5 h, 6 M HCl (1.58 mL) was added to the mixture to adjust the pH to 10. After removal of the solvent at reduced pressure, the residue was dissolved in DMF (35 mL). Then, 1-hydroxybenzotriazole (4.1 g, 30.5 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.7 g, 30.5 mmol) and 4-methoxybenzyl amine (3.76 mL, 25.4 mmol) were added. After stirring at room temperature for 17 h, water was 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, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc) to give the title compound (1.46 g, 84%) as a yellow gum:

Provenance & Evidence