Benzyl 4-(2-amino-4-fluoro-5-nitrophenyl)-2,2-dimethylbut-3-ynoate → Benzyl 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-(2-amino-4-fluoro-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (20.0 g, 56 mmol) in acetonitrile (100 mL) was added PdCl2 (5.0 g, 28 mmol) at room temperature. The mixture was stirred at 80° C. overnight. The mixture was filtered off and the solvent was evaporated in vacuo, the residue was purified by chromatography on silica gel (10% EtOAc in petroleum ether) to give benzyl 2-(6-fluoro-5-nitro-1H-indol-2-yl)-2-methylpropanoate (18.0 g, 90%). 1H NMR (300 MHz, CDCl3) 8.96 (br s, 1 H), 8.33 (d, J=7.2 Hz, 1 H) 7.35-7.28 (m, 5 H) 7.08 (d, J=11.7 Hz, 1 H), 6.47 (s, 1 H), 5.18 (s, 2 H) 1.69 (s, 6 H).

Provenance & Evidence