Trifluoroacetic acid → 3-chloro-5-[(6-chloro-2-fluoro-3-{[6-(methyloxy)-1-oxo-1,3,4,9-tetrahydro-2H-beta-carbolin-2-yl]methyl}phenyl)oxy]benzonitrile

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Reaction Steps

1,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-β-carboline-9-carboxylate (0.03 g, 0.05 mmol), was dissolved in CH2Cl2 (1.0 mL) and TFA (1.0 mL) was added dropwise. The reaction mixture was stirred 1 h and the solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized with saturated NaHCO3 and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.02 g, 80%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.50 (br. s., 1H), 7.80 (s, 1H), 7.47-7.55 (m, 3H), 7.39 (t, 1H), 7.27 (d, 1H), 7.04 (d, 1H), 6.86 (dd, 1H), 4.76 (s, 2H), 3.75 (s, 3H), 3.66 (t, 2H), 2.97 (t, 2H). MS: m/z 510.2 (M+1).

Provenance & Evidence