Methyl iodide → HCID 25261140, compound

HRID 1625202Notes

Reaction equation

HRID 1625202 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)=[O:10])=[C:7]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[Cl:32])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].IC.[C:37]([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([C:5]1[CH:23]=[CH:22][C:8]([C:9]([N:11]([CH3:37])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=2)=[O:10])=[C:7]([O:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[Cl:32])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 25260976HCID 25260976, compound

Product 1

HCID 25261140HCID 25261140, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-tert-butyl-2-(2-chloro-4-fluorophenoxy)-N-(3-(methylsulfonyl)phenyl)benzamide (14 mg, 30 μmol) in 0.30 mL DMF was added NaH (60% suspension in mineral oil, 3 mg, 80 μmol). After 5 min, iodomethane (5 μL, 80 μmol) was added to the reaction, and it was stirred for 16 h at room temperature. The reaction was worked up by adding sat. NaHCO3(aq) and extracting with CH2Cl2. The organic layer was filtered through a pad of Na2SO4 and evaporated. The product, 4-tert-butyl-2-(2-chloro-4-fluorophenoxy)-N-methyl-N-(3-(methylsulfonyl)phenyl)benzamide, was purified using reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). LC/MS: m/z 490.2 (M+H)+ at 2.03 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionextracting with CH2Cl2
  2. filtrationThe organic layer was filtered through a pad of Na2SO4
  3. customevaporated
  4. customThe product, 4-tert-butyl-2-(2-chloro-4-fluorophenoxy)-N-methyl-N-(3-(methylsulfonyl)phenyl)benzamide, was purified
  5. waitLC/MS: m/z 490.2 (M+H)+ at 2.03 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record
ord-369dfb2c1dad49c4bcc83c0aea5d40f6
Source dataset
uspto-grants-2014_07
Patent number
US08779197B2

Reaction notes

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