Potassium Carbonate → HCID 58042474, compound

HRID 2048088Notes

Reaction equation

HRID 2048088 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13](F)[C:12]([Cl:16])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl:17][C:18]1[CH:19]=[C:20]([OH:27])[CH:21]=[N:22][C:23]=1[CH:24]1[CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[OH-].[Na+]>[Cl:1][C:2]1[CH:14]=[C:13]([O:27][C:20]2[CH:21]=[N:22][C:23]([CH:24]3[CH2:26][CH2:25]3)=[C:18]([Cl:17])[CH:19]=2)[C:12]([Cl:16])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58042388HCID 58042388, compoundHCID 580424875-Chloro-6-cyclopropylpyridin-3-OL

Product 1

HCID 58042474HCID 58042474, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl 2,5-dichloro-4-fluorobenzoate (Preparation 218, 251 mg, 0.61 mmol) was added to a solution of 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 161 mg, 0.61 mmol) and potassium carbonate (393 mg, 1.82 mmol) in dimethylsulfoxide (5 mL). The reaction mixture was stirred at room temperature for 18 hours then diluted with sodium hydroxide (1M, 5 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with heptane:dichloromethane (from 95:5 to 60:40) to afford the title compound as a colourless oil (116 mg, 30%).

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by silica gel column chromatography
  6. washeluting with heptane

Sources & evidence

ORD record
ord-06f040bb41a647fabd5686af0c19da59
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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