2,6-Lutidine → 1h-Indole-2-carboxylic acid,3-phenyl-1-[[4-(phenylamino)phenyl]methyl]-

Participants

Reaction Steps

Phenylboronic acid (0.16 g, 0.81 mmol), Cu(OAc)2 (0.049 g, 0.27 mmol), and myristic acid (0.037 g, 0.16 mmol) were combined in a 100-mL round-bottom flask with a large stir bar. A rubber septum was attached, and dry toluene (2 mL), 2,6-lutidine (0.066 mL, 0.57 mmol), and 1-(4-amino-benzyl)-3-phenyl-1H-indole indolecarboxylic acid ethyl ester (0.20 g, 0.54 mmol) were successively added. The resulting mixture was stirred at a high rate for 24 h, diluted with ethyl acetate (10 mL), filtered through a plug of silica gel, and then purified by column chromatography (5 to 25% EtOAc/hexanes) to give a gummy solid. To a stirred solution of the gummy solid in 15 mL of 2:1:1 THF/MeOH/water was added lithium hydroxide monohydrate (0.1 g, 2.4 mmol). The reaction was stirred at 40° C. for 5 h. Most of the organic solvents was removed and the reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and purified by HPLC as a white powder (0.023 g, 10%): 1H NMR (DMSO-d6) δ 5.64 (s, 2H), 6.77 (t, J=7.4 Hz, 1H), 6.96 (d, J=8.5 Hz, 2H), 7.00 (dd, J=7.6, 0.9 Hz, 2H), 7.04(t, J=7.1 Hz, 1H), 7.15-7.19(m, 4H), 7.25 (t, J=7.11 Hz, 1H), 7.39 (t, J=7.4 Hz, 2H), 7.46-7.53 (m, 1H), 7.53 (t, J=7.4 Hz, 2H), 7.54-7.56 (m, 2H), 8.08 (br s, 1H), 13.01 (br s, 1H); MS (ESI) m/z 419 (MH+); MS (ESI) m/z 417 ([M−H]−); HRMS calcd for C28H23N2O2: 419.1757; found (ESI+): 419.1755.

Provenance & Evidence