Potassium Hydroxide → [7-(4-Benzyl-[1,2,3]triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-acetic acid

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Reaction Steps

To a stirred solution of propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl]acetate (1 eq) in THF/MeOH (2:1, 0.1M) at room temperature was added a 2M solution of potassium hydroxide (10 eq) The reaction mixture was stirred at room temperature for 2 h then quenched by adding HCl 10% until acidic pH and diluted with dichloromethane (DCM). Filtration through a phase separator followed by evaporation afforded the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1 H), 8.05 (s, 1 H), 7.46 (d, 1 H), 7.40 (d, 1 H), 7.34-7.17 (m, 5 H), 7.12-7.00 (m, 2 H), 5.35-5.18 (m, 1 H), 4.67 (dd, 1 H), 4.32 (dd, 1 H), 4.02 (s, 2 H), 3.69-3.50 (m, 2 H), 3.07-2.92 (m, 2 H), 2.52-2.30 (m, 2 H). MS (+ESI) m/z: 387.2.

Provenance & Evidence