Methyl iodide → HCID 118500493, compound

HRID 712732Notes

Reaction equation

HRID 712732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH3:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:19]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:10]([CH3:19])[S:11]([CH2:14][CH3:15])(=[O:12])=[O:13])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118500702HCID 118500702, compound

Product 1

HCID 118500493HCID 118500493, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a vial is added ethanesulfonic acid [(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-amide (180 mg, 0.61 mmol) in 3 ml of THF, followed by the addition of NaH (35 mg, 0.92 mmol). Then iodomethane (131 mg, 0.92 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 116 mg of ethanesulfonic acid [(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-methyl-amide.

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-72dacf41f5c5458dab091da927e0f83e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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