Water → HCID 9797039, compound

HRID 380975Notes

Reaction equation

HRID 380975 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][CH:3]=1.[CH:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)=[O:17].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1>[CH:16]([C:18]1[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 9860843HCID 9860843, compound

Product 1

HCID 9797039HCID 9797039, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a degassed solution of 1.5 g (5.1 mmol) of material from Example 1, 1.2 g (8.1 mmol) of 3-formylbenzeneboronic acid and 1.1 g (8.1 mmol) of potassium carbonate in 30 mL of toluene was added 0.3 g (0.3 mmol) of tetrakis-(triphenylphosphine)palladium(0). The mixture was heated to 100° C. for 16 hours whereupon 5 mL of water was added and heating continued for 1 hour. The mixture was then cooled to ambient temperature and 10 mL of water was added. The organic portion was separated and the aqueous portion was extracted twice with ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography on 50 g silica gel (40% ethyl acetate/hexane) afforded 0.7 g (41%) of the title compound.

Workup

  1. additionwas added
  2. temperatureheating
  3. customThe organic portion was separated
  4. extractionthe aqueous portion was extracted twice with ethyl acetate
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-953dd173c9244ea386a94c82fc8a171f
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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