1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → HCID 25066207, compound

Participants

Reaction Steps

In the same manner as in the synthesis of Compound 457, Compound 19 shown in Reaction 5 and (1-(tert-butoxycarbonyl)-1H-pyrrole-2-yl)boronic acid were subjected to the Suzuki reaction to obtain N-(4-(1H-pyrrole-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide. Thus obtained N-(4-(1H-pyrrole-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide (20 mg, 0.05 mmol) was dissolved in methanol (3 ml), and NaOMe (30 μl, 0.5 mmol, 1.0 M/tetrahydrofuran) was added thereto at room temperature. The mixture was refluxed with stirring for 3 hours at 80° C. After completion of the reaction, the reaction mixture was cooled to room temperature, and diluted with an EtOAc solution. The organic layer was washed with water, and brine. The extracted organic layer was dried over anhydrous MgSO4, and the solid substance was filtered off. The filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/1→1/2) to obtain Compound 597 (8 mg, 45%) in a form of a yellow solid.

Provenance & Evidence