Methyl iodide → HCID 21963995, compound

HRID 2212381Notes

Reaction equation

HRID 2212381 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:24])[CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:35]I>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])[CH2:12][CH2:13][CH:14]([CH2:17][C:18](=[O:24])[CH:19]([S:20]([CH3:23])(=[O:22])=[O:21])[CH3:35])[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21963994HCID 21963994, compound

Product 1

HCID 21963995HCID 21963995, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The product from Example 134 (28 mg, 0.056 mmol) in 1,2-dimethoxyethane (3 mL) was treated with sodium hydride (60% dispersion in mineral oil, 2 mg, 0.056 mmol) at room temperature. After stirring for 1.5 hours, methyl iodide (6 μL, 0.056 mmol) was added and the reaction stirred for 18 hours, then quenched with saturated aqueous ammonium chloride solution. The reaction was then extracted into ethyl acetate, dried (MgSO4) and evaporated to a white solid which was purified by column chromatography on silica eluting with 35% ethyl acetate/iso-hexane to yield the desired product as a white solid (13 mg).

Workup

  1. stirringthe reaction stirred for 18 hours
  2. customquenched with saturated aqueous ammonium chloride solution
  3. extractionThe reaction was then extracted into ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated to a white solid which
  6. customwas purified by column chromatography on silica eluting with 35% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-2aa2ccfdb59441e59fb1bc56a0b84656
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

Loading…