Water → HCID 86690641, compound

HRID 1505606Notes

Reaction equation

HRID 1505606 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:21][C:22]([F:25])([F:24])[F:23])[S:10]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])(=[O:12])=[O:11])=[C:4]([F:26])[CH:3]=1.[H-].[Na+].I[CH3:30].O>CN(C)C(=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:21][C:22]([F:23])([F:24])[F:25])[S:10]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH3:30])[CH3:14])(=[O:12])=[O:11])=[C:4]([F:26])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86690640HCID 86690640, compound

Product 1

HCID 86690641HCID 86690641, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)ethanesulfonamide (307 mg, 0.67 mmol) in N,N-dimethylacetamide (5 mL) was added sodium hydride (60% in mineral oil) (33 mg, 0.81 mmol) and the reaction was stirred at ambient temperature for 1 hour. Iodomethane (0.063 mL, 1.0 mmol) was then added and the reaction was stirred at 75° C. for 16 hours. LCMS analysis showed a 1:1 mixture of starting material and product. Water was added and the reaction was diluted with EtOAc, washed with brine (×2), dried with MgSO4, concentrated an purified by silica gel column chromatography (0-10% EtOAc in heptane) to give 249 mg of an inseparable mixture of starting material and product. The mixture was used for the next step. LCMS (m/z) ES+ 471 [M+18]+ (starting material); LCMS (m/z) ES+ 485 [M+18]+ (product).

Workup

  1. stirringthe reaction was stirred at 75° C. for 16 hours
  2. additiona 1:1 mixture of starting material and product
  3. washwashed with brine (×2)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customan purified by silica gel column chromatography (0-10% EtOAc in heptane)

Sources & evidence

ORD record
ord-8bfba060028c451d933317eb9962924b
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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