Sodium Carbonate → HCID 18437414, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of bis-benzo[1,3]dioxol-5-ylmethyl-(3-butyl-2-iodo-5-phenyl-3H-imidazol-4-ylmethyl)-amine (62 mg, 0.1 mmol) and Pd(PPh3)4 (6 mg) in 1 ml of toluene is added aqueous sodium carbonate (0.4 ml of 2.0 N) and 2-methylphenyl boronic acid (18 mg, 0.13 mmol, 1.3 eq.) in 0.3 ml of ethanol under nitrogen, the resulting mixture is stirred at 100° C. for 8 h. After being cooled to room temperature, the reaction mixture is diluted with 10 ml of ethyl acetate, washed with water and brine and dried over sodium sulfate. Concentration and purification by flash chromatography affords 43 mg of bis-benzo[1,3]dioxol-5-ylmethyl-(3-butyl-5-phenyl-2-o-tolyl-3H-imidazol-4-ylmethyl)-amine 1H NMR (400 MHz, CDCl3) δ 7.70 (2H, d, J=7.2 Hz), 7.43˜7.24 (7H, m), 6.77˜6.67 (6H, m), 5.94 (4H, s), 3.87 (2H, t, J=7.6 Hz), 3.78(2H, s), 3.37 (4H, s), 2.20 (3H,s), 1.17 (2H, m), 0.88 (2H, m), 0.63 (3H, t, J=7.2 Hz); MS (+VE) m/z 588 (M+1).

Provenance & Evidence