Methyl iodide → N-(1-{[2-Chloro-4-(methyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide

HRID 1946373Notes

Reaction equation

HRID 1946373 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])=[N:11]1.[CH3:26]C(C)([O-])C.[K+].CI>CS(C)=O.CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:26])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[C:17]2[C:18]([F:24])=[CH:19][CH:20]=[CH:21][C:22]=2[F:23])=[N:11]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59547950N-{1-[(2-Chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide

Product 1

HCID 59547989N-(1-{[2-Chloro-4-(methyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of N-{1-[(2-chloro-4-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide (for a preparation see Example 31)(30 mg, 0.082 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (9.6 mg, 0.086 mmol) and then methyl iodide (6 μl, 0.096 mmol, Aldrich). The solution was stirred at ambient temperature overnight. The solution was diluted with methanol (0.5 ml) and purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a colourless gum (7.3 mg); LCMS: (System 4) MH+=378, tRET=2.85 min.

Workup

  1. custompurified by MDAP on Sunfire C18 column
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b77bbbe8d8144ec59923b6112dbdb7c3
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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