Sodium Carbonate → 4-Ethyl-3-(pyridin-3-yl)benzaldehyde

HRID 2113132Notes

Reaction equation

HRID 2113132 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH3:11])[CH:5]=[O:6].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:10]([C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:14]1[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=1)[CH3:11]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 222596893-Bromo-4-ethylbenzaldehyde

Product 1

HCID 223911924-Ethyl-3-(pyridin-3-yl)benzaldehydeYield 49.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 3-bromo-4-ethylbenzaldehyde (2.45 g, 0.0115 mol), pyridine 3-boronic acid (1.42 g, 0.0115 mol, Matrix Scientific), 2M Na2CO3 (15 mL) in 30 mL of toluene was added 1.33 g of Pd (PPh3)4 (1.15 mmol, Aldrich). The mixture was then heated to 80 C under N2 for 16 hours. The mixture was cooled to RT and was diluted with 100 mL of EtOAc and 40 mL of sat. NaHCO3 aq. solution. The organic phase was washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude product was chromatographed (silica gel, 20% EtOAc in hexane) to provide yellow oil (1.2 g).

Workup

  1. temperatureThe mixture was then heated to 80 C under N2 for 16 hours
  2. washThe organic phase was washed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed (silica gel, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-52f2ff7d43c54a38807e952620733d2b
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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