Hydrochloric Acid → HCID 86621087, compound

HRID 1620828Notes

Reaction equation

HRID 1620828 reaction equation
Br[C:2]1O[C:5]([CH2:7][N:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O)=[O:12].[C:22](=O)([O-])[O-].[Na+].[Na+].Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[CH3:9][N:8]([CH2:7][C:5]1[CH2:22][C:2]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:11]=[O:12])=[CH:3][CH:4]=1)[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 12329868HCID 12329868, compound

Product 1

HCID 86621087HCID 86621087, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial, (5-bromo-furan-2-ylmethyl)-dimethyl-amine (385 mg, 1.88 mmol), 2-formyl phenylboronic acid (288 mg, 1.93 mmol) and 3.7 ml of actonitrile were mixed. Then, 3.7 ml of 1N aqueous sodium carbonate was added to the mixture, followed by 5 mole percent of dichlorobis(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150° C. for 5 minutes with microwave irradiation. After cooling, 20 ml of 1N HCl was added. The mixture was extracted by ethyl acetate (3×10 ml) and the ethyl acetate layer was discarded. 1N NaOH solution was added to aqueous phase to adjust pH to 10, then extracted with ethyl acetate (3×20 ml). The combined organic layer was washed with water and dried over sodium sulfate. The solvent was evaporated to give 300 mg of 2-(4-dimethylaminomethyl-cyclopenta-1,3-dienyl)-benzaldehyde, yield: 69%.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. extractionThe mixture was extracted by ethyl acetate (3×10 ml)
  4. addition1N NaOH solution was added to aqueous phase
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. washThe combined organic layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-617889f5bf044d779ea01677eecb1e6f
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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