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

HRID 1159882Notes

Reaction equation

HRID 1159882 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C: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.CCOC(C)=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 59511407HCID 59511407, compound

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 8857Ethyl AcetateSolvent

Procedure

N-[3-(2-Chloro-pyrimidin-4-ylethynyl)-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 heated in DMSO (175 mL) were reacted according to earlier examples to afford, after workup, 7.45 g of the title compound, Rf=0.2 (2:1 Hex/EtOAc).

Workup

  1. customwere reacted
  2. customto afford

Sources & evidence

ORD record
ord-d3c4dc3ac15440e2993c882e865151da
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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