Water → HCID 86690639, compound

HRID 1505604Notes

Reaction equation

HRID 1505604 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[C:4]([F:20])[CH:3]=1.[H-].[Na+].FC(F)(F)S(O[CH2:29][C:30]([F:33])([F:32])[F:31])(=O)=O.O>CN(C)C(=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:29][C:30]([F:33])([F:32])[F:31])[S:10]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[C:4]([F:20])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 86690638HCID 86690638, compound

Product 1

HCID 86690639HCID 86690639, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-methanesulfonamide (4.21 g, 11.8 mmol) in N,N-dimethylacetamide (40 mL) was added sodium hydride (60% in mineral oil) (611 mg, 15.3 mmol) and the reaction was stirred at ambient temperature for 30 minutes. 2,2,2-Trifluoroethyl trifluoromethanesulfonate (2.0 mL, 14.1 mmol) was then slowly added (exothermic) and the reaction was stirred at ambient temperature for 2.5 hours. Water was added and the reaction was diluted with EtOAc, washed with water (×2), brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-100% EtOAc in heptane) to give N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide (4.62 g, 89% yield). LCMS (m/z) ES+ 457 [M+18]+.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 2.5 hours
  2. washwashed with water (×2), brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-7a416ec50cec486f80e67fd8ea98e7c3
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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