Potassium Carbonate → N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

HRID 1157532Notes

Reaction equation

HRID 1157532 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[CH:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=1.[I-].[NH2:24][N+:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[K+].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH:13]=[CH:14][CH:15]=3)=[N:24][N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=23)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 86631082N-[3-(2-Chloro-pyrimidin-4-ylethenyl)-phenyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 59513717N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamideYield 63.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

N-[3-(2-Chloro-pyrimidin-4-ylethenyl)-phenyl]-2,2,2-trifluoro-acetamide (9.14 g, 28.1 mmol), N-aminopyridinium iodide (6.24 g, 28.1 mmol), KOH (1.57 g, 28.9 mmol) and K2CO3 (7.76 g) were stirred in DMSO (175 mL) until all starting material was consumed by LC/MS analysis. Reaction was poured into water to yield a precipitate which was filtered off, washed well with water and dried. Crude product was triturated in EtOAc and filtered to yield 7.45 g of the title compound, Rf=0.2 (2:1 Hexanes/EtOAc).

Workup

  1. customwas consumed by LC/MS analysis
  2. customReaction
  3. customto yield a precipitate which
  4. filtrationwas filtered off
  5. washwashed well with water
  6. customdried
  7. customCrude product was triturated in EtOAc
  8. filtrationfiltered

Sources & evidence

ORD record
ord-67ede9aba3ac41aabfb5716a749c397c
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…