Potassium Carbonate → HCID 17974502, compound

HRID 2252331Notes

Reaction equation

HRID 2252331 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.F[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 17974502HCID 17974502, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-pyridin-3-ol (418 mg, 3.2 mmol), 2-fluorobenzaldehyde (522 mg, 4.21 mmol), potassium carbonate (442 mg, 3.2 mmol) and copper powder (201 mg, 3.2 mmol) was heated in DMF (6.4 mL) at 120° C. for 6 hours. The reaction was then cooled, and concentrated to an oil. The residue was purified by flash chromatography (eluting with 20% ethyl acetate/hexane) to give the title compound as a brown solid (700 mg, 93%).

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated to an oil
  3. customThe residue was purified by flash chromatography (eluting with 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ce5bf0dfaf99411ea222aa68cb57c169
Source dataset
uspto-grants-2008_01
Patent number
US07321040B2

Reaction notes

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