Methyl iodide → HCID 68768313, compound

HRID 2067087Notes

Reaction equation

HRID 2067087 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:29])[C@H:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:28])=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:15][CH:14]=1)[CH3:11].[H-].[Na+].[CH3:32]I>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:32])[C:9](=[O:29])[C@H:10]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:28])=[CH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:15][CH:14]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68523335HCID 68523335, compound

Product 1

HCID 68768313HCID 68768313, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.4 g (1 mmol) of the compound obtained in Example 38 was dissolved in anhydrous tetrahydrofuran, and the mixture was cooled to 0° C. 40 mg (1 mmol) of 60% NaH and 0.14 g (1 mmol) of methyliodide were sequentially added to the reaction mixture, and the mixture was stirred at room temperature for 5 hours. Ice was added to the reaction mixture and resulting mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure. The resulting residue was subjected to column chromatography (ethyl acetate:n-hexane=1:2) to obtain the title compound (300 mg, 73.3%).

Workup

  1. additionIce was added to the reaction mixture
  2. customresulting mixture
  3. extractionwas extracted three times with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-98249ebf137e4f269d4857d58b19237a
Source dataset
uspto-grants-2012_10
Patent number
US08293774B2

Reaction notes

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