Methyl iodide → HCID 70665008, compound

HRID 1403629Notes

Reaction equation

HRID 1403629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:26]([O:28][CH3:29])=[O:27])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:33]>O1CCCC1.[NH4+].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH3:33])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:26]([O:28][CH3:29])=[O:27])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664876HCID 70664876, compound

Product 1

HCID 70665008HCID 70665008, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-[(pyridin-2-ylmethyl)amino]quinoxaline-6-carboxylate (200 mg, 0.51 mmol) in tetrahydrofuran (50 mL) was added NaH (107 mg, 4.65 mmol) at 0° C., and the reaction mixture was stirred for 30 minutes. Iodomethane (954 mg, 6.72 mmol) was added, and the reaction mixture was stirred overnight at room temperature. The resulting solution was diluted with NH4Cl solution (80 mL), extracted with ethyl acetate (3×40 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give methyl 2-(4-fluorophenyl)-3-[methyl(pyridin-2-ylmethyl)amino]quinoxaline-6-carboxylate as a yellow solid (120 mg, 57%).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ec46a8b15604afab0afb1499c334c41
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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