Methyl iodide → HCID 70664627, compound

HRID 1403547Notes

Reaction equation

HRID 1403547 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([NH:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]([O:27][CH2:28]C)=[O:26])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32]I>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]([CH3:32])[CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]([O:27][CH3:28])=[O:26])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664736HCID 70664736, compound

Product 1

HCID 70664627HCID 70664627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-fluorophenyl)-3-(tetrahydro-2H-pyran-4-ylamino)quinoxaline-6-carboxylate (180.0 mg, 0.47 mmol) in tetrahydrofuran (20 mL) was added sodium hydride (22.7 mg, 0.95 mmol) at 0° C. and stirred for 1 h at room temperature. Then CH3I (134.0 mg, 0.94 mmol) was added at 0° C. and stirred overnight at room temperature. The reaction mixture was quenched by the addition of NH4Cl solution (100 ml) and adjusted to pH 6 with hydrochloric acid (1N), extracted with dichloromethane (3×30 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum to afford methyl 2-(4-fluorophenyl)-3-(methyl(tetrahydro-2H-pyran-4-yl)amino)quinoxaline-6-carboxylate as yellow oil (100 mg, crude).

Workup

  1. stirringstirred overnight at room temperature
  2. customThe reaction mixture was quenched by the addition of NH4Cl solution (100 ml)
  3. extractionextracted with dichloromethane (3×30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-70f2a0a04c2f48869c88881f22764205
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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