Water → 3-(2-Fluoro-pyridin-4-yl)-benzaldehyde

HRID 14933Notes

Reaction equation

HRID 14933 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.C(OB([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)O)=O.[C:20](=O)([O-])[O-:21].[K+].[K+].O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:19]=[C:14]([CH:15]=[CH:16][CH:17]=2)[CH:20]=[O:21])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 70235702-Fluoro-4-iodopyridineHCID 66687538Formylphenylboronic acid

Product 1

HCID 866033173-(2-Fluoro-pyridin-4-yl)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 fluoro-4-iodo pyridine (5 g), 3 formylphenylboronic acid (4 g), and palladium tetrakis triphenylphosphine were suspended in 500 mL of THF. Potassium carbonate (7.42 g) was added along with 50 mL of water. The flask was purged with nitrogen and the mixture heated to 65 C for 4 hours. The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate and water. Removal of the ethyl acetate gave a residue which was chromatographed on silica gel (1:1 ethyl acetate hexanes) to give the desired product. Yield: 1.42 g. LC-MS showed the product had the expected M+H+ of 202.

Workup

  1. customThe flask was purged with nitrogen
  2. temperaturethe mixture heated to 65 C for 4 hours
  3. customThe solvent was removed by rotary evaporation
  4. customthe residue partitioned between ethyl acetate and water
  5. customRemoval of the ethyl acetate
  6. customgave a residue which
  7. customwas chromatographed on silica gel (1:1 ethyl acetate hexanes)

Sources & evidence

ORD record
ord-ca97ba8058b64914b78c231d37fd98b7
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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