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

HRID 512056Notes

Reaction equation

HRID 512056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].Br[CH2:12][C:13]1[C:23]([F:24])=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:25])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH2:12][C:13]2[C:23]([F:24])=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:25])[CH:14]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 666673833-Chloro-5-hydroxy-2-methoxypyridineHCID 66667533Ethyl 4-(bromomethyl)-2,5-difluorobenzoate

Product 1

HCID 66667744Ethyl 4-((5-chloro-6-methoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoateYield 51.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-chloro-6-methoxypyridin-3-ol (Preparation 56, 98 mg, 0.612 mmol) in acetone (10 mL) were added ethyl 4-(bromomethyl)-2,5-difluorobenzoate (Preparation 19, 171 mg, 0.612 mmol) and potassium carbonate (170 mg, 1.224 mmol). The mixture was stirred for 18 hours at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with water (20 mL), and extracted with DCM (2×30 mL). Combined organic extracts were dried over sodium sulphate, and evaporated to a yellow solid. The solid was purified by silica gel chromatography eluting with DCM/heptanes (3:2) to afford the title compound as a white solid (112 mg, 51%).

Workup

  1. extractionextracted with DCM (2×30 mL)
  2. dry with materialCombined organic extracts were dried over sodium sulphate
  3. customevaporated to a yellow solid
  4. customThe solid was purified by silica gel chromatography
  5. washeluting with DCM/heptanes (3:2)

Sources & evidence

ORD record
ord-1b71d13de4074b71bc628094f6d84139
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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