Water → HCID 58042480, compound

HRID 2048115Notes

Reaction equation

HRID 2048115 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[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+].O>CS(C)=O>[Cl:1][C:2]1[C:3]([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)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 580424875-Chloro-6-cyclopropylpyridin-3-OLHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 58042480HCID 58042480, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 59, 35.7 g, 143.86 mmol) in DMSO (97.6 mL) was added 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 69, 24.4 g, 143.86 mmol) and stirred at room temperature until a solution obtained. Potassium carbonate (49.7 g, 359.65 mmol) was added portion wise maintaining the internal temperature at 15-25° C. with a cold water jacket. The reaction mixture was stirred at room temperature for 12 hours, cold water charged and the resulting slurry stirred for 90 minutes. The mixture was filtered, washed with water and dried to give the title compound as a pale yellow solid (54.0 g, 94%).

Workup

  1. customobtained
  2. stirringThe reaction mixture was stirred at room temperature for 12 hours
  3. stirringthe resulting slurry stirred for 90 minutes
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-402152241ad647f79baa56189bf86c68
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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