Potassium Carbonate → 4-(4-Bromofuran-2-yl)pyridine

HRID 2109461Notes

Reaction equation

HRID 2109461 reaction equation
Br[C:2]1[O:3][C:4]([Si](C)(C)C)=[C:5]([Br:7])[CH:6]=1.[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:7][C:5]1[CH:6]=[C:2]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)[O:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 576342652,4-Dibromo-5-(trimethylsilyl)furan

Product 1

HCID 576342534-(4-Bromofuran-2-yl)pyridineYield 42.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Procedure

2,4-Dibromo-5-(trimethylsilyl)furan (8.97 g), pyridine-4-boronic acid (1.85 g, 15.1 mmol), potassium carbonate (6.24 g, 45.2 mmol) and tetrakis(triphenylphosphine)palladium (0) (435 mg, 0.38 mmol) were heated under refluxed in ethanol/1,2-dimethoxyethane (1:4 v/v; 100 mL) at 100° C. for 6 h. The solution was allowed to cool, and was then filtered and evaporated. The residue was purified by flash chromatography using a gradient of ethyl acetate in hexane to give the title compounds as a pale brown solid (1.45 g), m/z 224, 226 (MH+).

Workup

  1. temperatureto cool
  2. filtrationwas then filtered
  3. customevaporated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-85a2c01b1eb14dbfb57a07a5aed702e9
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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