Methyl iodide → HCID 57467659, compound

HRID 404394Notes

Reaction equation

HRID 404394 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 methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-(hydroxymethyl)cyclopentyl)benzoate (75.0 mg, 209.0 μmol) at 0° C. The resulting mixture was stirred at room temperature for 30 minutes and then methyl iodide (296.0 mg, 2087 μmol) was added to the reaction mixture. The resulting mixture was stirred at room temperature overnight. EtOAc (60.0 mL) was added, and the organic layers were washed with brine (20×2 mL) and dried over MgSO4. The product was obtained after filtration and solvent removal. The product was used in the next step. MS ESI (pos.) m/e: 374.0 (M+H)+.

Workup

  1. customat 0° C
  2. stirringThe resulting mixture was stirred at room temperature overnight
  3. washthe organic layers were washed with brine (20×2 mL)
  4. dry with materialdried over MgSO4
  5. customThe product was obtained
  6. filtrationafter filtration and solvent removal

Sources & evidence

ORD record
ord-ff4259171bc64833b8190f5c07d3cace
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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