Sodium Hydroxide → 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxyamide

HRID 388515Notes

Reaction equation

HRID 388515 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.CC(C)([O-])C.[K+].Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][C:25]([NH2:27])=[O:26])[CH:19]=1.[OH-].[Na+]>CS(C)=O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][C:25]([NH2:27])=[O:26])[CH:19]=2)=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27787624-Amino-2,5-difluorophenolHCID 220403482-(4-Chloro-2-pyridinyl)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 1317302204-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxyamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After dissolving 4-amino-2,5-difluorophenol (4.95 g) in dimethyl sulfoxide (50 ml) under a nitrogen stream, potassium tert-butoxide (4.05 g) was added at room temperature and the mixture was stirred for 25 minutes. After adding 4-chloropyridine-2-carboxyamide (2.70 g) to the mixture, stirring was continued at 80° C. for 2.5 hours. After cooling the reaction mixture to room temperature, a 1N aqueous solution of sodium hydroxide (74.25 ml) was added and stirring was continued for 10 hours. The precipitated solid was collected by filtration and washed with water. The solid was dried with warm air at 100° C. for 24 hours to give the title compound (3.38 g, 74%) as purple powder.

Workup

  1. additionwas added at room temperature
  2. stirringstirring
  3. waitwas continued at 80° C. for 2.5 hours
  4. stirringstirring
  5. waitwas continued for 10 hours
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. customThe solid was dried
  9. temperaturewith warm air at 100° C. for 24 hours

Sources & evidence

ORD record
ord-2de51cd7129a49b6bfd9894cccd7d6c7
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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