Methyl iodide → HCID 57467659, compound

HRID 1662508Notes

Reaction equation

HRID 1662508 reaction equation
[H-].[Na+].[F:3][C:4]1[C:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[C:22]2([CH2:27][OH:28])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.CI.[CH3:31]COC(C)=O>CN(C=O)C>[F:3][C:4]1[C:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[C:22]2([CH2:27][O:28][CH3:31])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57467658HCID 57467658, compound

Product 1

HCID 57467659HCID 57467659, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (20.0 mg 60% in oil, 522 μmol) in DMF (1.0 mL) was slowly added 77.12A (75.0 mg, 209.0 μmol) at 0° C. The resulting mixture was stirred at room temperature for 30 minutes. Methyl iodide (296.0 mg, 2087 μmol) was then added, and the reaction was stirred for 16 hours at room temperature. EtOAc (60.0 mL) was added, and the mixture was washed with brine (20×2 mL) and dried over MgSO4. The solvent was removed. The product was used in the next step without further purification. MS ESI (pos.) m/e: 374.0 (M+H)+.

Workup

  1. customat 0° C
  2. stirringthe reaction was stirred for 16 hours at room temperature
  3. washthe mixture was washed with brine (20×2 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed
  6. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-143e5677fa1f47f19ab916aa8b66d228
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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