HCID 59129384, compound → HCID 59129495, compound

Participants

Reaction Steps

To a deoxygenated solution of methyl 4-(2-butyramido-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (1.8 g, 5.4 mmol) in acetonitrile (30 mL) was added Pd(CH3CN)2Cl2(0.42 g, 1.6=mmol) under N2. The mixture was heated at reflux for 24 h. After cooling the mixture to ambient temperature, the solid was filtered off and washed with EtOAc (50 mL×3). The filtrate was evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=30/1) to give methyl 2-methyl-2-(5-nitro-1H-indol-2-yl)propanoate (320 mg, 23%). 1 H NMR (400 MHz, CDCl3) δ 9.05(brs, 1H), 8.52(d, J=2.0 Hz, 1 H), 8.09(dd, J=2.0, 8.8 Hz, 1 H), 7.37(d, J=8.8 Hz, 1 H), 6.54(d, J=1.6 Hz, 1 H), 3.78(d, J=9.6 Hz, 3 H), 1.70(s, 6 H).

Provenance & Evidence