Water → 4-(4-Ethoxyphenyl)pyridine

HRID 409733

Reaction equation

HRID 409733 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[CH3:17].O>O1CCOCC1.CO>[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:10]2[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=2)=[CH:21][CH:20]=1)[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2207001-Ethoxy-4-iodobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 707009334-(4-Ethoxyphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Under inert gas atmosphere 88 mg (0.12 mmol) PdCl2(dppf)xCH2Cl2, 13.6 mL (27.2 mmol) 2N sodium carbonate solution and 1.64 g (13.3 mmol) pyridine-4-boronic acid are added to 3.00 g (12.1 mmol) 1-ethoxy-4-iodo-benzene in 18 mL 1,4-dioxane and 6 mL methanol. The mixture is stirred for 2 d at reflux. After that time, water is added. The precipitate is filtered off, taken up in DCM and extracted with water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; gradient DCM:MeOH 100:0->95:5) to yield the desired product which is directly used in the next reaction step.

Workup

  1. temperatureat reflux
  2. filtrationThe precipitate is filtered off
  3. extractionextracted with water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silica gel; gradient DCM:MeOH 100:0->95:5)

Sources & evidence

ORD record
ord-0773c6064e154ae6a9f6b0133b2f14be
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Linked notes

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