Ethyl 5-phenylthiazole-2-carboxylate → (S)-Methyl 3-methyl-2-(1-oxo-6-(4-(5-phenylthiazole-2-carboxamido)phenyl)isoindolin-2-yl)butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of the compound of example 6 (405 mg, 1.2 mmol) and ethyl 5-phenylthiazole-2-carboxylate (233 mg, 1 mmol) in toluene (15 mL) in a sealed tube, was added 2M solution of AlMe3 (135 mg, 1.875 mmol) and the reaction mixture was heated at 80° C. for 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with saturated ammonium chloride. The resulting solution was extracted with ethyl acetate. The ethyl acetate extract was washed with water, brine, dried over anhydrous sodium sulphate and concentrated to obtain a crude material, which was purified using column chromatography (30% ethyl acetate in petroleum ether) to afford the title compound.

Provenance & Evidence