Water → HCID 86721865, compound

HRID 1049005Notes

Reaction equation

HRID 1049005 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.O>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 101309Benzenesulfonamide, p-bromo-N-isobutyl-

Product 1

HCID 86721865HCID 86721865, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-bromo-N-isobutyl-benzenesulfonamide (0.25 g, 856 μmol) in anhydrous dimethylacetamide (5 mL) was added NaH (60% dispersion in mineral oil, 37.7 mg, 942 μmol) and the mixture was stirred at room temperature for 15 minutes. 4-Fluorobenzyl bromide (117 μL, 942 μmol) was added and reaction heated at 90° C. for 2 hours. The reaction was left to cool to room temperature, water added and then extracted with DCM, filtered through a phase separator, concentrated and purified by silica gel column chromatography (0-25% DCM in cyclohexane) to give 4-bromo-N-(4-fluoro-benzyl)-N-isobutyl-benzenesulfonamide (267 mg, 78%) 1H NMR (300 MHz, CDCl3): δ 7.65-7.66 (m, 4H), 7.23 (m, 2H), 6.99 (t, 2H), 4.27 (s, 2H), 2.89 (d, 2H), 1.64 (dt, 1H), 0.74 (d, 6H).

Workup

  1. customreaction
  2. temperatureheated at 90° C. for 2 hours
  3. waitThe reaction was left
  4. temperatureto cool to room temperature
  5. extractionextracted with DCM
  6. filtrationfiltered through a phase separator
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (0-25% DCM in cyclohexane)

Sources & evidence

ORD record
ord-a8ff6e9e5d414d789269d81ec61e4ce1
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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