Methyl iodide → HCID 11772916, compound

HRID 1768458Notes

Reaction equation

HRID 1768458 reaction equation
[CH2:1]([CH:4]1[O:21][C:20]2[C:15](=[C:16]([O:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[C:14]2[C:5]1=[C:6]1[C:11](=[CH:12][CH:13]=2)[NH:10][C:9]([CH3:25])([CH3:24])[C:8](=[O:26])[NH:7]1)[CH:2]=[CH2:3].[C:27](=O)([O-])[O-].[Cs+].[Cs+].CI>CC#N.O>[CH2:1]([CH:4]1[O:21][C:20]2[C:15](=[C:16]([O:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[C:14]2[C:5]1=[C:6]1[C:11](=[CH:12][CH:13]=2)[NH:10][C:9]([CH3:25])([CH3:24])[C:8](=[O:26])[N:7]1[CH3:27])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11210289HCID 11210289, compound

Product 1

HCID 11772916HCID 11772916, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of xiii (10 mg, 0.029 mmol) in CH3CN (1 mL) was added cesium carbonate (14 mg, 0.043 mmol) and methyl iodide (3.5 mL, 0.57 mmol) and the mixture was stirred at room temperature for 12 hours. The mixture was diluted with water (10 mL) and extracted with EtOAc (3×10 mL). The organic extracts were combined, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by preparative thin layer chromatography to provide compounds xv (6.2 mg, 60%).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-8120bd0e5d7344d7810dec2bb95eb842
Source dataset
uspto-grants-2007_06
Patent number
US07235662B2

Reaction notes

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