Potassium Carbonate → HCID 58042396, compound

HRID 2048058Notes

Reaction equation

HRID 2048058 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:5]=[N:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 66666494HCID 66666494, compound

Product 1

HCID 58042396HCID 58042396, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

5-Chloro-6-(trifluoromethyl)pyridin-3-ol (Preparation 83, 250 mg, 1.266 mmol) was added to a solution of 4-fluorobenzaldehyde (150 mg, 1.209 mmol) and potassium carbonate (260 mg, 1.881 mmol) in DMSO (5 mL). The mixture was stirred at 85° C. for 18 hours, then at 125° C. for 72 hours. The mixture was diluted with EtOAc (15 mL) and washed with water (2×10 mL). The organic layer was dried over sodium sulfate, filtrated and concentration in vacuo. The crude oil was purified by silica gel chromatography eluting with 0 to 20% EtOAc in heptane to yield the title compound as a yellow oil (26.5 mg, 70%):

Workup

  1. waitat 125° C. for 72 hours
  2. washwashed with water (2×10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentration in vacuo
  6. customThe crude oil was purified by silica gel chromatography
  7. washeluting with 0 to 20% EtOAc in heptane

Sources & evidence

ORD record
ord-ba2fd9a3e8244d378554005c6064a06a
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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