Methyl iodide → HCID 117667429, compound

HRID 712740Notes

Reaction equation

HRID 712740 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11](=[O:13])[CH3:12])[CH3:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:17]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:10]([CH3:17])[C:11](=[O:13])[CH3:12])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117667398HCID 117667398, compound

Product 1

HCID 117667429HCID 117667429, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a vial is added N-[(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-acetamide (111 mg, 0.46 mmol) in 3 ml of THF, followed by the addition of 60% NaH (35 mg, 0.92 mmol). Then iodomethane (130 mg, 0.91 mmol) is added. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is diluted with DCM, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 103 mg of N-[(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-N-methyl-acetamide.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-576372ea1fcf42bcb144878307785df7
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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