Cesium carbonate → HCID 11644124, compound

HRID 270738Notes

Reaction equation

HRID 270738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:17]=[CH:16][C:15](C)=[CH:14][N:13]=1.[C:19](=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1)(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>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 5642162-Bromo-5-methylpyridineHCID 2734323(3-Chlorophenyl)boronic acidHCID 11667372HCID 11667372, compound

Product 1

HCID 11644124HCID 11644124, compound

Reagents, catalysts & solvents 2

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

Procedure

10.0 g (0.064 mol) of 3-Chlorophenylboronic acid, 13.20 g (0.077 mol) of 2-bromo-5-methyl-pyridine, 20.84 g (0.064 mol) of cesium carbonate, 1.47 g (0.0016 mol) of tris(dibenzylideneacetone) dipalladium (0), 1.33 g (0.0038 mol) of di-tert-butyl-pyren-1-yl-phosphane and 100 ml of dioxane were refluxed at room for 12 hours. The reaction mixture was filtered and the solvent was removed under vacuum. The resulting mixture was purified by distillation in vacuum. Yield of 2-(3-chloro-phenyl)-4-methyl-pyridine was 7.09 g (45%) with b.p. at 114° C./0.1 mm. 1H NMR (CD2Cl2) 2.56 (s, 3H, Me) 7.40-8.80 (m, 7H, arom-H). Anal. Calcd. for C12H10ClN (Mol. Wt.: 203,67): C, 70,77; H, 4,95; N, 6,88. Found: C, 70,93; H, 5,14; N, 6,95. The structure has been confirmed by X-ray analysis.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum
  3. distillationThe resulting mixture was purified by distillation in vacuum
  4. customat 114° C.

Sources & evidence

ORD record
ord-aca6b48c7d104712bf3929dbb0fa9b1a
Source dataset
uspto-grants-2008_11
Patent number
US07449601B2

Reaction notes

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