Hydrogen Peroxide → {4-[1-(4-Fluorophenyl)-3-methyl-1H-pyrazol-5-yl]}pyridine-2-carboxamide

HRID 1635504Notes

Reaction equation

HRID 1635504 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH3:21])[CH:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].OO.C(=O)([O-])[O-:25].[K+].[K+].O>CS(C)=O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([C:1]([NH2:2])=[O:25])[CH:8]=3)=[CH:10][C:11]([CH3:21])=[N:12]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 186761072-Cyano-4-[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Product 1

HCID 9948119{4-[1-(4-Fluorophenyl)-3-methyl-1H-pyrazol-5-yl]}pyridine-2-carboxamideYield 628.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-cyano-4-[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 32; 1.0 g, 0.0036 mol) in 25 mL of DMSO was added hydrogen peroxide (0.43 mL, 0.0036 mol) and potassium carbonate (0.072 g, 0.00051 mol) at zero degrees C. The reaction mixture was warmed up to room temperature over 1 hour. Water was added and the mixture was stirred for 0.5 hours. The resulting precipitate was collected by filtration to give 0.95 g (89% yield) of product as a pale yellow solid: mp: 168-170° C.; Anal. Calc'd. for C16H13FN4O: C, 64.86; H, 4.42; N, 18.91. Found: C, 64.48; H, 4.27; N, 18.80.

Workup

  1. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-042213646dd84cf1a79cf85eddd1b1f0
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

Loading…