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

HRID 2243563Notes

Reaction equation

HRID 2243563 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCOCC1>[CH3:21][C:19]1[CH:18]=[CH:17][N:16]=[C:15]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([Si:2]([CH3:13])([CH3:12])[CH3:1])[CH:4]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27340872-Bromo-4-methylpyridineHCID 45771813-(Trimethylsilyl)phenylboronic acid

Product 1

HCID 592113504-Methyl-2-(3-trimethylsilanyl-phenyl)-pyridine

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under 1 mm vacuum
  3. distillationThe resulting mixture was purified by distillation in vacuum

Sources & evidence

ORD record
ord-ee567a23491e45c1bf39090b504fa1ca
Source dataset
uspto-grants-2010_03
Patent number
US07675228B2

Reaction notes

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