Potassium Carbonate → HCID 58042461, compound

HRID 2048119Notes

Reaction equation

HRID 2048119 reaction equation
[CH:1]1([C:4]2[N:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=2[O:11][C:12]([F:15])([F:14])[CH3:13])[CH2:3][CH2:2]1.[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Cl:16][C:17]1[C:18]([O:10][C:7]2[CH:8]=[N:9][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:5]([O:11][C:12]([F:15])([F:14])[CH3:13])[CH:6]=2)=[CH:19][C:20]([F:30])=[C:21]([CH:29]=1)[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58042378HCID 58042378, compoundHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 58042461HCID 58042461, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A suspension of 6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-ol (Preparation 269, 155 mg, 0.72 mmol), tert-butyl 5-chloro-2,4-difluorobenzoate (179 mg, 0.72 mmol) and potassium carbonate (299 mg, 2.16 mmol) in dimethyl sulfoxide (3 mL) was stirred for 4 hours at room temperature. The reaction mixture was diluted with water (40 mL) then extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with 5% diethyl ether in heptane to afford the title compound as a white solid (260 mg, 81%).

Workup

  1. extractionthen extracted with ethyl acetate (3×30 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 5% diethyl ether in heptane

Sources & evidence

ORD record
ord-750209d06621479dba9cfd5d28cd8117
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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