Ethyl Acetate → HCID 11533851, compound

Participants

Reaction Steps

140 mg 4-Allyl-1-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-1H-pyrrolo[2,3- b]pyridin-5-ol were dissolved in 10 ml dimethylformamide and 195 mg cesium carbonate and 116 mg tert.-butylbromoacetate were added. The reaction mixture was stirred at room temperature for two hours when 100 ml ethyl acetate were added and the mixture was washed five times with portions of 20 ml of water The organic layer was dried over MgSO4 and the solvent removed under reduced pressure. The residue was dissolved in 10 ml dichloromethane and 4 ml trifluoroacetic acid were added. The reaction mixture was stirred at room temperature for three hours then 100 ml toluene were added and the solvents removed under reduced pressure. The residue was dissolved in 20 ml methanol and 50 mg palladium (10% on charcoal) were added. The reaction mixture was stirred at room temperature in a hydrogen atmosphere (5 bar) for one hour. The catalyst was filtered off and the solvent removed under reduced pressure. The residue was purified by RP-HPLC to provide 70 mg {1-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-4-propyl-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-acetic acid as colorless lyophilisate.

Provenance & Evidence