Methyl iodide → HCID 66797584, compound

HRID 1020737Notes

Reaction equation

HRID 1020737 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH:6]=[N:5]2.[H-].[Na+].[CH3:23]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH3:23])[CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66797551HCID 66797551, compound

Product 1

HCID 66797584HCID 66797584, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
7.5 °C

Procedure

(6-Bromo-quinoxalin-2-yl)-(4-fluoro-benzyl)-amine (0.35 g, 1.0 mmol) was added to a suspension of sodium hydride (0.037 g, 1.5 mmol) in DMF (5 mL) at room temperature and it was stirred for 15 minutes. The reaction mixture was cooled down to 5-10° C. and methyl iodide (0.17 g, 1.2 mmol) was added at 5-10° C. and this was maintained for 30 minutes. After completion of the reaction, the reaction mixture was gradually poured into ice cold water (30 mL) and stirred for a further 30 minutes. The precipitated product was filtered and washed by water and dried under vacuum to afford the title compound (0.4 g) which was used directly for the next step.

Workup

  1. temperaturethis was maintained for 30 minutes
  2. customAfter completion of the reaction
  3. stirringstirred for a further 30 minutes
  4. filtrationThe precipitated product was filtered
  5. washwashed by water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4f0646ee838c472fb1b9edaf2c065479
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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