Methyl iodide → HCID 70664709, compound

HRID 1403632Notes

Reaction equation

HRID 1403632 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].I[CH3:31]>O1CCCC1>[CH:1]1([N:6]([CH3:31])[C:7]2[C:8]([C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[N:9][C:10]3[C:15]([N:16]=2)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70664643HCID 70664643, compound

Product 1

HCID 70664709HCID 70664709, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(cyclopentylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.55 mmol) in tetrahydrofuran (15 mL) was added sodium hydride (96 mg, 4.00 mmol) at 0° C. After stirring for 1 h at room temperature, iodomethane (141.94 mg, 1.00 mmol) was added at 0° C. and the reaction mixture was stirred overnight. The reaction was then quenched by the addition of water (3 mL), extracted with dichloromethane (3×15 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give methyl 3-(cyclopentyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow oil (120 mg, crude).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe reaction was then quenched by the addition of water (3 mL)
  3. extractionextracted with dichloromethane (3×15 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b22ec52efca4d639ad5dceb2ca5195e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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