Cesium carbonate → 4-Methyl-2-(3-trimethylsilanyl-phenyl)-pyridine

Participants

Reaction Steps

15.0 g (0.0773 mol) of 3-trimethylsilyl-phenylboronic acid, 11.96 g (0.0695 mol) of 2-bromo-4-methyl-pyridine, 30.21 g (0.0927 mol) of cesium carbonate, 0.71 g (0.000776 mol) of tris(dibenzylideneacetone) dipalladium (0), 0.38 g (0.00188 mol) of tri-tert-butyl-phosphane and 100 ml of dioxane were stirred at room temperature for 12 hr. The reaction mixture was filtered and the solvent was removed under 1 mm vacuum. The resulting mixture was purified by distillation in vacuum. Yield of 4-methyl-2-(3-trimethylsilanyl-phenyl)-pyridine was 8.18 g (48.75%) as a colorless liquid with b.p. 89-90° C./0.02. 1H NMR (CD2Cl2) 0.30 (s, 9H, Me3Si), 2.32 (s, 3H, Me) 7.00-8.55 (m, 7H, arom-H). Anal. Found: C, 74.65; H, 7.94; N, 5.88.

Provenance & Evidence