methyl 1H-indole-5-carboxylate → HCID 57263143, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of NaOMe [prepared in-situ from sodium metal (0.261 g, 11.36 mmol) in MeOH (10 mL) at 60° C.] was added hydroxyguanidine (0.863 g, 11.36 mmol) and the resulting mixture was stirred at 60° C. for 30 min. To the above mixture, methyl 1H-indole-5-carboxylate (1 g, 5.68 mmol) was added and the reaction was stirred at 60° C. for 12 h. The reaction was cooled to RT and quenched with H2O (100 mL). The aqueous layer was extracted in EtOAc (2×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by triturating with pentane to give 5-(1H-indol-5-yl)-[1,2,4]oxadiazol-3-ylamine (0.1 g, 8.6%) as an off-white solid. MS (ESI, pos. ion) m/z: 201.1 (M+1). 1H-NMR (400 MHz DMSO-d6): δ 11.53 (s, —1H), 8.24 (s, 1H), 7.73 (dd, J=11.6, 2.4 Hz, 1H), 7.56 (m, 2H), 6.61 (s, 1H), 6.29 (s, 2H).

Provenance & Evidence