Methyl iodide → HCID 59547883, compound

HRID 1946360Notes

Reaction equation

HRID 1946360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:26])=[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

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59547885HCID 59547885, compound2×

Product 1

HCID 59547883HCID 59547883, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-{1-[(2-chloro-5-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide (for as preparation see Intermediate 13) (73 mg, 0.20 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (21 mg, 0.187 mmol). The reaction was stirred for 5 min before adding methyl iodide (0.012 mL, 0.201 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 (10.5 mg); LCMS: (System 4) MH+=378, tRET=2.86 min.

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-e396760adf7e48ef97d304f195ccd447
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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