Methyl iodide → HCID 86630438, compound

HRID 1667577Notes

Reaction equation

HRID 1667577 reaction equation
[CH:1]1([S:4][C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:2]1.[C:19](=O)([O-])[O-].[K+].[K+].CI>CC#N.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([S:4][C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][N:8]([CH3:19])[C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57448163HCID 57448163, compound

Product 1

HCID 86630438HCID 86630438, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

To 1C (1.68 g, 5.47 mmol) in CH3CN (55 mL) was added potassium carbonate (1.13 g, 8.20 mmol), tetrabutylammonium bromide (88 mg, 0.27 mmol) and methyl iodide (3.40 mL, 54.7 mmol) and the reaction was heated to reflux overnight. After cooling to rt and concentrating, the remaining residue was dissolved in ethyl acetate and washed with water (3×) and brine. The organic layer was dried (MgSO4), filtered and concentrated to provide ID (1.50 g) as a yellow oil. LC-MS: 321.95 (M+H)+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrating
  4. dissolutionthe remaining residue was dissolved in ethyl acetate
  5. washwashed with water (3×) and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto provide ID (1.50 g) as a yellow oil

Sources & evidence

ORD record
ord-e91ff95fcddf44798980bb24f6af2bfe
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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