Methyl iodide → 4-bromo-2-fluoro-N-methyl-N-(pyrimidin-2-ylmethyl)benzamide

HRID 595811Notes

Reaction equation

HRID 595811 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:7])=[C:4]([F:18])[CH:3]=1.[H-].[Na+].I[CH3:22]>CN(C=O)C>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]([CH3:22])[CH2:9][C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:15]=2)=[O:7])=[C:4]([F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1180457014-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamide

Product 1

HCID 1180455744-bromo-2-fluoro-N-methyl-N-(pyrimidin-2-ylmethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask was charged with 4-bromo-2-fluoro-N-(pyrimidin-2-ylmethyl)benzamide (74.5 mg, 0.24 mmol), NaH (60% dispersion in mineral oil, 11.5 mg, 0.288 mmol) in DMF (2 mL), to the slurry was added iodomethane (20 μl, 0.312 mmol) and to the resulting mixture was stirred at room temperature for 10 min, then was quenched by water (20 μl), concentrated and the crude residue was dissolved in EtOAc, washed with water, and brine, dried (Na2SO4), concentrated and 4-bromo-2-fluoro-N-methyl-N-(pyrimidin-2-ylmethyl)benzamide was obtained as oil (55.3 mg, 71%). LCMS (m/z): 324.1/326.1 (MH+), 0.66 min.

Workup

  1. customwas quenched by water (20 μl)
  2. concentrationconcentrated
  3. dissolutionthe crude residue was dissolved in EtOAc
  4. washwashed with water, and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9cac57ba2d0a49c9b5f38b1e329977ea
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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