HCID 117700269, compound → Methyl 6-ethyl-1H-indole-2-carboxylate

Participants

Reaction Steps

Methyl 2-azido-3-(4-ethylphenyl)acrylate (36) (1.0 g, 4.33 mmol) was dissolved in p-xylene and heated at reflux for 3 h. After evaporation of the solvent, the residue was purified by flash column chromatography eluting with a linear gradient ranging from 0 to 20% EtOAc-hexanes to provide 0.52 g (59%) of product 37 as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.28 (t, J=7 Hz, 3H), 2.79 (q, J=7 Hz, 2H), 3.94 (s, 3H), 7.03 (dd, J=2, 8 Hz, 1H), 7.17-7.18 (m, 1H), 7.21-7.23 (m, 1H), 7.60 (d, J=8 Hz, 1H), 8.78 (s, 1H). LC-MS (CI): m/z 202.0 [(M−H)− C12H13NO2 requires 203.09].

Provenance & Evidence