Methyl iodide → HCID 59547867, compound

HRID 1946379Notes

Reaction equation

HRID 1946379 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[N:8]=1)=[O:5].[CH3:29]C(C)([O-])C.[K+].CI>CS(C)=O>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:29])=[CH:15][C:14]=2[C:20]([F:23])([F:21])[F:22])[N:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59547990HCID 59547990, compound

Product 1

HCID 59547867HCID 59547867, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,6-difluoro-N-(1-{[4-hydroxy-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 36)(72 mg, 0.181 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (20 mg, 0.178 mmol). The reaction mixture was stirred for 5 min before adding methyl iodide (0.011 ml, 0.181 mmol, Aldrich). The reaction was stirred at ambient temperature, overnight and under nitrogen. The reaction mixture was filtered through a hydrophobic frit and the filtrate diluted with methanol (0.5 ml) and the sample 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 white solid (20.3 mg);

Workup

  1. stirringThe reaction was stirred at ambient temperature, overnight and under nitrogen
  2. filtrationThe reaction mixture was filtered through a hydrophobic frit
  3. additionthe filtrate diluted with methanol (0.5 ml)
  4. customthe sample purified by MDAP on Sunfire C18 column
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0f05e9a9687442e5af18d696e774b107
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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