Methyl iodide → HCID 77230301, compound

HRID 912931Notes

Reaction equation

HRID 912931 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])[CH:7]=[N:8][C:9]=1[Cl:10].I[CH3:17]>CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]([CH3:17])[C:13](=[O:15])[CH3:14])[CH:7]=[N:8][C:9]=1[Cl:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19959722N-(5,6-Dichloro-pyridin-3-ylmethyl)-acetamide

Product 1

HCID 77230301HCID 77230301, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (41 mg, 1.0 mmol, Aldrich, 60% dispersion in mineral oil) was added portionwise to a solution of N-(5,6-dichloro-pyridin-3-ylmethyl)-acetamide (150 mg, 0.68 mmol, Example 155d) and iodomethane (0.063 mL, 1.0 mmol, Aldrich) in DMF (3.0 mL) with stirring at room temperature. The mixture was stirred for 30 min at room temperature, diluted with EtOAc (30 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 80% EtOAc/hexane to give the title compound. MS (ESI, pos. ion) m/z: 233 (M+1).

Workup

  1. stirringThe mixture was stirred for 30 min at room temperature
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with 80% EtOAc/hexane

Sources & evidence

ORD record
ord-4a41baca59a246cfa3af0c35a30ed3d8
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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