Methyl iodide → HCID 90266389, compound

HRID 1483170Notes

Reaction equation

HRID 1483170 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:16][C@H:15]3[C@H:10]([NH:11][CH2:12][CH2:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:16][C@H:15]3[C@H:10]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 90266388HCID 90266388, compound

Product 1

HCID 90266389HCID 90266389, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 23a (600 mg, 2.13 mmol) was dissolved in acetonitrile. Potassium carbonate (590 mg, 4.26 mmol) and iodomethane (652 mg, 3.20 mmol) were added. The resulting mixture was allowed to react overnight at 80° C. and monitored by TLC. After the reaction completed, it was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic phase was washed with saturated saline solution, and dried over anhydrous sodium sulfate. Column chromatography afforded 405 mg of white solid (compound 23b), yield 64%.

Workup

  1. customto react overnight at 80° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-a93971f490894790adffec7e5f467063
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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