Acetic Acid → Ammonium Hydroxide

Participants

Reaction Steps

3-(5-Chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzonitrile (Example 14, 200 mg, 0.56 mmol) in acetic acid (3 mL) is added to a 20% HCl aqueous solution (3 mL). The reaction mixture is refluxed for 3 days. The volatiles are removed in vacuo and the residue is redissolved in methanol and purified by reverse phase HPLC with Xbridge Shield RP18 and a gradient of 0.1% NH4OH in acetonitrile to give 3-(5-chloro-3-methyl-2-pyridin-3-yl-indol-1-ylmethyl)-benzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.21 (s, 3H), 5.36 (s, 2H), 6.83 (d, J=7.1 Hz, 1H), 7.13-7.23 (m, 2H), 7.43-7.52 (m, 3H), 7.64-7.70 (m, 2H), 7.74-7.81 (m, 1H), 8.55 (s, 1H), 8.61-8.62 (m, 1H). HRMS (ESI) m/z 377.1058 [(M+H)+ Calcd for C22H18ClN2O2: 377.1057].

Provenance & Evidence