Potassium Carbonate → tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

HRID 1525660Notes

Reaction equation

HRID 1525660 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:20]=[C:19](F)[C:18]([F:22])=[CH:17][C:9]=1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][OH:32])[CH:27]=[N:28][C:29]=1[Cl:30]>CS(C)=O>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][O:32][C:19]2[C:18]([F:22])=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:8]([F:7])[CH:20]=2)[CH:27]=[N:28][C:29]=1[Cl:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10868153Tert-butyl 2,4,5-trifluorobenzoateHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoateYield 97.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium carbonate (535 mg, 3.88 mmol) was added to a solution of tert-butyl 2,4,5-trifluorobenzoate (Preparation 10, 275 mg, 1.29 mmol) and (5,6-dichloropyridin-3-yl)methanol (241 mg, 1.36 mmol) in DMSO (5 mL). The reaction mixture was stirred at RT for 18 hours. After cooling the reaction mixture was quenched with water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (2×100 mL) and dried over MgSO4, filtered and concentrated in vacuo to give 490 mg of the title compound in a quantitative yield. The crude compound was used without further purification.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas quenched with water (25 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3e8d395c6704a84a1ba36f479fed947
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

Loading…