Sodium Carbonate → HCID 69231128, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1-benzyl-3-bromo-5-nitro-1H-indole-2-carboxylate (0.40 g, 1 mmol), 4-tert-butylbenzeneboronic acid (0.36 g, 2 mmol), 2 M aqueous sodium carbonate (5 mL), tetrakis(triphenylphosphine)palladium (0) (0.20 g, 0.17 mmol) in ethanol (5 mL) and toluene (5 ml) was heated at 65° C. for 16 h and then cooled. The reaction mixture was diluted with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and concentrated. Flash silica gel chromatography using 5˜25% ethyl acetate/hexane gave 0.41 g (90%) of ethyl 1-benzyl-3-(4-tert-butylphenyl)-5-nitro-1H-indole-2-carboxylate as a yellowish solid: 1H NMR (DMSO-d6) δ 0.92 (t, J=7.0 Hz, 3H, 1.36 (s, 9H, 4.10 (q, J=7.0 Hz, 2H, 5.89 (s, 2H, 7.09 (d, J=8.4 Hz, 2H, 7.22-7.45 (m, 3H, 7.95 (d, J=7.6 Hz, 2H, 7.54 (d, J=8.5 Hz, 2H, 7.91 (d, J=11.2 Hz, 1H, 8.22 (dd, J=11.2, 2.1 Hz, 1H, 8.37 (d, J=2.1 Hz, 1H; MS (ESI) m/z 457 (MH+); HRMS calcd for C28H29N2O4: 457.2128; found (ESI+): 457.2114; Anal. calcd for C28H28N2O4: C, 73.66; H, 6.18; N, 6.14. Found: C, 73.48; H, 6.30; N, 5.97.

Provenance & Evidence