A mixture of 12 (0.403 g, 0.001 mol), 2-methoxyphenylboronic acid (0.182 g, 0.0012 mol),
tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.0001 mol), toluene (18 mL), methanol (3.6 mL) and
2M potassium carbonate (1 mL) was refluxed for 16 h under argon atmosphere. The reaction mixture was
cooled to rt and washed with 10 mL of a saturated aqueous solution of ammonium chloride. The organic
layer was dried over anhydrous sodium sulfate and evaporated. The residue was subjected to column
chromatography with ethyl acetate/n-hexane (2+8). The product was recrystallized from ethanol to give
0.362 g (84%) of 14; mp 88 - 93°C; MS: m/z (rel. int.) 430 (M+, 13), 371 (13), 314 (17), 226 (22), 73
(100); 1H-NMR (CDCl3): δ = 8.47 - 8.29 (m, 2H, ArH), 8.07 - 7.82 (m, 4H, ArH), 7.78 (s, 1H, ArH), 7.61
- 7.44 (m, 2H, ArH), 7.33 - 7.18 (m, 1H, ArH), 7.16 - 6.93 (m, 2H, ArH), 5.39 (s, 2H, NCH2-), 3.99 (s,
3H, -OCH3), 3.69 (t, J = 8.1 Hz, 2H, -OCH2CH2-), 0.99 (t, J = 8.1 Hz, 2H, -OCH2CH2-), 0.02 (s, 9H, -
13
Si(CH3)3); C-NMR (CDCl3): δ = 156.0 (ArC), 147.5 (ArC), 136.7 (ArC), 133.2 (ArC), 133.1 (ArC),
128.5 (ArCH), 128.3 (ArCH), 128.2 (ArCH), 127.7 (ArC), 127.7 (ArCH), 127.7 (ArCH), 127.4 (ArCH),
126.6 (ArCH), 126.6 (ArCH), 126.3 (ArCH), 122.6 (ArC), 121.7 (ArCH), 120.9 (ArCH), 110.5 (ArCH),
75.5 (NCH2-), 66.3 (-OCH2CH2-), 55.2 (-OCH3), 17.7 (-OCH2CH2-), -1.4 (-Si(CH3)3); Anal. Calcd for
C26H30N2O2Si: C, 72.52; H, 7.02; N, 6.51. Found: C, 72.73; H, 6.78; N, 6.28.
2-(4-Biphenyl)-4-(4-ethylphenyl)-1-{[2-(1,1,1-trimethylsilyl)ethoxy]methyl}-1H-imidazole (15)
A mixture of 13 (0.429 g, 0.001 mol), 4-ethylphenylboronic acid (0.180 g, 0.0012 mol),
tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.0001 mol), toluene (18 mL), methanol (3.6 mL) and
2M potassium carbonate (1 mL) was refluxed for 16 h under argon atmosphere. The reaction mixture was
cooled to rt and washed with 10 mL of a saturated aqueous solution of ammonium chloride. The organic
layer was dried over anhydrous sodium sulfate and evaporated. The residue was subjected to column
chromatography with ethyl acetate/n-hexane (2+8). The product was recrystallized from isopropanol to
give 0.355 g (78%) of 15; mp 135 - 141°C; MS: m/z (rel. int.) 454 (4), 396 (14), 337 (7), 73 (100), 45 (8);
1H-NMR (CDCl3): δ = 7.99 - 7.18 (m, 14H, ArH), 5.34 (s, 2H, NCH2-), 3.65 (t, J = 8.2 Hz, 2H, -
OCH2CH2-), 2.68 (q, J = 7.6 Hz, 2H, CH3CH2-), 1.27 (t, J = 7.6 Hz, 3H, CH3CH2-), 0.97 (t, J = 8.2 Hz,
2H, -OCH2CH2-), 0.02 (s, 9H, -Si(CH3)3); 13C-NMR (CDCl3): δ = 148.4 (ArC), 143.0 (ArC), 141.6
(ArC), 141.5 (ArC), 140.4 (ArC), 131.4 (ArC), 129.4 (ArCH), 129.1 (ArC), 128.8 (ArCH), 128.0
(ArCH), 127.6 (ArCH), 127.2 (ArCH), 127.1 (ArCH), 125.0 (ArCH), 116.7 (ArCH), 75.6 (NCH2-), 66.4
(-OCH2CH2-), 28.6 (CH3CH2-), 17.8 (-OCH2CH2-), 15.6 (CH3CH2-), -1.4 (-Si(CH3)3); Anal. Calcd for
C29H34N2OSi: C, 76.61; H, 7.54; N, 6.16. Found: C, 76.36; H, 7.64; N, 6.11.
4-(2-Methoxyphenyl)-2-(2-naphthyl)-1H-imidazole (16)