Potassium Carbonate → HCID 58042507, compound

HRID 2048083Notes

Reaction equation

HRID 2048083 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:8].[Cl:20][C:21]1[CH:22]=[C:23]([OH:30])[CH:24]=[N:25][C:26]=1[CH:27]1[CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[C:3]([O:30][C:23]2[CH:24]=[N:25][C:26]([CH:27]3[CH2:29][CH2:28]3)=[C:21]([Cl:20])[CH:22]=2)=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580424875-Chloro-6-cyclopropylpyridin-3-OLHCID 58042518HCID 58042518, compound

Product 1

HCID 58042507HCID 58042507, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 26, 0.330 g, 1.168 mmol) was added portionwise over 5 minutes to a suspension of 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 0.214 g, 1.262 mmol) and potassium carbonate (0.32 g, 2.315 mmol) in DMSO (5.0 mL). The mixture was stirred at room temperature for 3 hours, then partitioned between water (20.0 mL) and tert-butyl methyl ether (20.0 mL). The organic layer was further washed with water (2×20.0 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 0 to 5% EtOAc in heptane to yield the title compound as a white solid (0.289 g, 0.668 mmol, 57%):

Workup

  1. custompartitioned between water (20.0 mL) and tert-butyl methyl ether (20.0 mL)
  2. washThe organic layer was further washed with water (2×20.0 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified with silica gel chromatography
  7. washeluting with 0 to 5% EtOAc in heptane

Sources & evidence

ORD record
ord-5e6c6c5ad7b24bdc93512f3b9c4aab48
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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