Potassium Carbonate → HCID 86637430, compound

HRID 2265797Notes

Reaction equation

HRID 2265797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH2:32]Br.[F:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[C:39]([F:43])[C:40]=1[O:41][CH3:42].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.[Pd](Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:32][C:37]1[CH:36]=[C:35]([F:34])[C:40]([O:41][CH3:42])=[C:39]([F:43])[CH:38]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 17750046(3,5-Difluoro-4-methoxyphenyl)boronic acidHCID 68421570HCID 68421570, compound

Product 1

HCID 86637430HCID 86637430, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred mixture of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-2-bromomethyl-benzene (0.30 g), 3,5-difluoro-4-methoxy-phenylboronic acid (0.21 g) and potassium carbonate (0.31 g) in acetone (3 mL) and water (1 mL) under argon is cooled in an ice-bath. Then palladium dichloride (5 mg) is added and the cooling bath is removed. The reaction mixture is stirred at ambient temperature overnight. Then brine is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried over sodium sulfate, and the solvent is removed in vacuo. The residue is taken up in methanol (5 mL) aqueous potassium hydroxide solution (1 mL, 4 mol/L) is added. The solution is stirred at ambient temperature for 0.5 h and then neutralized with 1 M hydrochloric acid. The methanol is evaporated, and the residue is diluted with brine and extracted with ethyl acetate. The organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->9:1).

Workup

  1. temperatureis cooled in an ice-bath
  2. customthe cooling bath is removed
  3. additionThen brine is added
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. customthe solvent is removed in vacuo
  7. additionis added
  8. stirringThe solution is stirred at ambient temperature for 0.5 h
  9. customThe methanol is evaporated
  10. additionthe residue is diluted with brine
  11. extractionextracted with ethyl acetate
  12. dry with materialThe organic extracts are dried over sodium sulfate
  13. customthe solvent is removed
  14. customThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->9:1)

Sources & evidence

ORD record
ord-99cde7447d44432fabb9b59f6977c4ef
Source dataset
uspto-grants-2010_12
Patent number
US07858587B2

Reaction notes

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