Sodium Hydroxide → 2-(3-Cyano-4-(5-(2,4-dichlorophenethylcarbamoyl)-1H-indol-1yl)phenyl)acetic Acid

Participants

Reaction Steps

To a stirred solution of methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate in methanol (1 mL) at ambient temperature was added aqueous sodium hydroxide (5.0 N, 0.036 mL) and 5 drops of water, and the reaction was stirred for 1 hour. The reaction mixture was taken up in DCM (5 mL) and washed with 2 M HCl (5 mL). The organic layer was dried over MgSO4 and concentrated to give the desired compound as a white solid 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.80 (s, 1H), 7.70 (dd, J=8.5, 2.1 Hz, 1H), 7.65 (d, J=8.6Hz, 1H), 7.57 (d, J=8.9 Hz, 1H), 7.44 (d, J=5.9 Hz, 1H), 7.32 (d, J=8.7 Hz, 1H), 7.17-7.25 (m, 3H), 6.82 (d, J=3.0 Hz, 1H), 6.24 (d, J=5.9 NH), 3.81 (s, 2H), 3.74 (q, J=6.6 Hz, 2H), 3.10 (t, J=7.0 Hz, 2H), MS(ESI)=492.3 (M+1).

Provenance & Evidence