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

HRID 595811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595811
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9cac57ba2d0a49c9b5f38b1e329977ea
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

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