Potassium Carbonate → HCID 69515307, compound

HRID 1593486Notes

Reaction equation

HRID 1593486 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[O:5][C:6]=1Br.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:10][C:8]([C:4]1[O:5][C:6]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)=[C:2]([Br:1])[CH:3]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 10616079tert-butyl 4,5-dibromo-2-furancarboxylate

Product 1

HCID 69515307HCID 69515307, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

tert-Butyl 4,5-dibromo-2-furancarboxylate (H. Muratake et al, Chem. Pharm. Bull., 1997, 45, 799) (9.78 g, 30 mmol), 4-pyridyl boronic acid (M. Lamothe et al, J. Med. Chem., 1997, 40, 3542) (4.06 g, 33 mmol), potassium carbonate (24.8 g, 180 mmol), triphenylphosphine (786 mg, 3 mmol) and palladium (II) acetate (337 mg, 1.5 mmol) were dissolved in ethylene glycol dimethyl ether (150 ml) and water (75 ml). The mixture was heated at reflux for 18 hours with vigorous stiring, cooled then filtered through celite pad, which was thoroughly washed with ethyl acetate. The filtrate was then washed with saturated sodium bicarbonate solution, water (×3) and brine, then dried over magnesium sulfate. The solution was evaporated in vacuo and the residue purified by silica gel chromatography to afford the title product (5.32 g, 55%); MS (AP−) m/e 323/325 [M−H]−.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 hours with vigorous stiring
  3. temperaturecooled
  4. filtrationthen filtered through celite pad, which
  5. washwas thoroughly washed with ethyl acetate
  6. washThe filtrate was then washed with saturated sodium bicarbonate solution, water (×3) and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solution was evaporated in vacuo
  9. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-1a4bb1ce13be41c6ad08b3d35d2e5363
Source dataset
uspto-grants-2007_11
Patent number
US07297693B2

Reaction notes

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