Potassium Carbonate → Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoate

HRID 512033Notes

Reaction equation

HRID 512033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].Br[CH2:15][C:16]1[C:25]([F:26])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:27])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:15][C:16]2[C:25]([F:26])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([F:27])[CH:17]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580425005-Chloro-6-isobutoxypyridin-3-OLHCID 66666576Benzoic acid, 4-(bromomethyl)-2,5-difluoro-, methyl ester

Product 1

HCID 66667691Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoateYield 89.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 5-chloro-6-isobutoxy-pyridin-3-ol (Preparation 1, 364 mg, 1.8 mmol) in DMSO (15 mL) was added methyl 4-(bromomethyl)-2,5-difluorobenzoate (Preparation 3, 479 mg, 1.8 mmol) followed by potassium carbonate (500 mg, 3.6 mmol) and the resulting mixture stirred at room temperature for 18 hours under nitrogen. The mixture was poured onto water (20 mL) and extracted with ethyl acetate (3×40 mL). The combined extracts were washed with water (20 mL), dried over magnesium sulphate, filtered and the solvent removed under reduced pressure to give the title compound (623 mg, 89%) as a light brown oil.

Workup

  1. additionThe mixture was poured onto water (20 mL)
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. washThe combined extracts were washed with water (20 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-70f9294efcb142499d33da66dd2939ae
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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