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

HRID 2386535Notes

Reaction equation

HRID 2386535 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-a52be17c35d94367859017ed1bcc3537
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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