Citric Acid → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Participants

Reaction Steps

To a solution of ethyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (130 mg, 0.291 mmol) in dioxane (2 mL) was added a 1 M LiOH aqueous solution (1.747 mL, 1.747 mmol). The reaction mixture was stirred at room temperature for 5 h, acidified to pH 3 with 0.5 M citric acid aqueous solution, and extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated to give the title compound as pink solid (110 mg). LCMS m/z=419.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (d, J=6.0 Hz, 6H), 2.25-2.35 (m, 1H), 2.41 (s, 3H), 2.67 (dd, J=16.5, 8.5 Hz, 1H), 2.88-2.98 (m, 2H), 3.73-3.81 (m, 1H), 3.97-4.04 (m, 1H), 4.10-4.16 (m, 1H), 4.62-4.68 (m, 1H), 4.97 (s, 2H), 6.17 (s, 1H), 6.84 (d, J=8.7 Hz, 1H), 6.97 (d, J=8.7 Hz, 1H), 7.01 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.6, 2.2 Hz, 1H), 7.63 (d, J=2.2 Hz, 1H).

Provenance & Evidence