Lithium Hydroxide → HCID 59864772, compound

Participants

Reaction Steps

Under an N2 atmosphere, methyl 2-(4-(4-(2,4-dichlorophenylsulfonamido)-2-methyl-1H-indol-5-yloxy)-2,3-dimethylphenyl)acetate (0.194 g, 0.354 mmol) was dissolved in tetrahydrofuran (2.5 mL) and 1N LiOH (aq) was added. The reaction was allowed to stir at room temperature for 2.5 h. The reaction was diluted with water and ethyl acetate. The layers were separated and the aqueous layer was made acidic with citric acid to pH 4 and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 8% methanol in dichloromethane, afforded the title compound. LC-MS EST (neg.) m/z: 531.1 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 10.94 (s, 1H); 9.75 (s, 1H); 7.53 (d, J=8.5 Hz, 1H); 7.48 (d, J=2.0 Hz, 1H); 7.20 (dd, J=8.5 Hz and 2.0 Hz, 1H); 7.07 (d, J=8.6 Hz, 1H); 6.72 (d, J=8.4 Hz, 1H); 6.27 (d, J=8.4 Hz, 1H); 6.13 (s, 1H); 5.99 (d, J=8.4 Hz, 1H); 3.50 (s, 2H); 2.35 (s, 3H); 2.09 (s, 3H); 1.92 (s, 3H).

Provenance & Evidence