Sodium Carbonate → HCID 58042702, compound

HRID 564053Notes

Reaction equation

HRID 564053 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16](Br)=[CH2:17])[C:11](=[O:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].C([O-])([O-])=O.[Na+].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:25]2[CH:26]=[CH:27][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=2)=[CH2:17])[C:11](=[O:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86623684HCID 86623684, compound

Product 1

HCID 58042702HCID 58042702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6.17 g (19.3 mmol) 4-benzyloxy-1-(2-bromo-allyl)-1H-pyridin-2-one (preparation 9a), 3.76 g (25.1 mmol) 4-formylphenylboronic acid and 1.56 g (1.35 mmol) tetrakis-triphenyl-phosphanepalladium in 150 ml 1,4-1,4-dioxanee and 45 mL MeOH is added 19.3 mL (38.5 mmol) 2M aqueous Na2CO3-solution under a nitrogen atmosphere. The reaction mixture is evacuated three times and flushed with nitrogen. The mixture is refluxed overnight under a nitrogen atmosphere and is diluted with water. The phases are separated and the aqueous phase is extracted with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. To the residue is added MeOH/acetonitrile, the mixture is filtered and purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Workup

  1. customThe reaction mixture is evacuated three times
  2. customflushed with nitrogen
  3. temperatureThe mixture is refluxed overnight under a nitrogen atmosphere
  4. additionis diluted with water
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with DCM
  7. dry with materialThe combined organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customthe solvent is evaporated
  10. additionTo the residue is added MeOH/acetonitrile
  11. filtrationthe mixture is filtered
  12. custompurified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90)

Sources & evidence

ORD record
ord-8a5f1c28876d405cb9ce874f1a88eed4
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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