Methyl iodide → HCID 58558255, compound

HRID 386828Notes

Reaction equation

HRID 386828 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][C:21](=O)C(F)(F)F)=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][CH3:21])=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 58755133N-[4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl]-2,2,2-trifluoroacetamide

Product 1

HCID 58558255HCID 58558255, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-2,2,2-trifluoroacetamide (0.59 mg, 1.3 mmol) in N,N-dimethylformamide (3 mL) was treated with potassium carbonate (0.28 g, 2.0 mmol) followed by methyl iodide (125 μL, 2 mmol) and stirred for 2 h. The reaction mixture was treated with additional methyl iodide (200 μL, 3.2 mmol) and stirred for 16 h. The reaction mixture was diluted with water (100 mL) and brine (25 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (3×100 mL) and brine (100 mL), dried with sodium sulfate, filtered, and concentrated to a crude residue which was purified by silica gel to give the desired product (0.39 g, 81%).

Workup

  1. stirringstirred for 16 h
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic extracts were washed with water (3×100 mL) and brine (100 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude residue which
  7. customwas purified by silica gel

Sources & evidence

ORD record
ord-68fe85129e2d45c981fbe4aca2b7897b
Source dataset
uspto-grants-2013_02
Patent number
US08372870B2

Reaction notes

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