Potassium Carbonate → HCID 58042433, compound

HRID 2048062Notes

Reaction equation

HRID 2048062 reaction equation
[F:1][C:2]1[CH:12]=[C:11](F)[C:10]([F:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:23]=[C:24]([OH:33])[CH:25]=[N:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:32])[CH3:31]>CS(C)=O.CCOC(C)=O>[Cl:21][C:22]1[CH:23]=[C:24]([O:33][C:11]2[C:10]([F:14])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[CH:12]=2)[CH:25]=[N:26][C:27]=1[O:28][CH2:29][CH:30]([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2774397Benzoic acid, 2,4,5-trifluoro-, ethyl esterHCID 580425005-Chloro-6-isobutoxypyridin-3-OL

Product 1

HCID 58042433HCID 58042433, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2,4,5-trifluorobenzoate (135 mg, 0.661 mmol) and potassium carbonate (156 mg, 1.129 mmol) were dissolved in DMSO (3.0 mL). 5-Chloro-6-isobutoxypyridin-3-ol (Preparation 16, 127.5 mg, 0.632 mmol) was added portion wise and the mixture was stirred at room temperature for 2 hours. The reaction was diluted in EtOAc (10.0 mL) and washed with brine (3×10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0 to 10% EtOAc in heptane to yield the title compound as a clear oil that solidified upon standing (155 mg, 35%):

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0 to 10% EtOAc in heptane

Sources & evidence

ORD record
ord-d4f1840cdae04bad8a02e1dad9a6cefd
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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