2-Fluoro-4-isopropenyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide → HCID 16752625, compound

HRID 2262602Notes

Reaction equation

HRID 2262602 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[CH:4][C:3]=1[S:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH3:28])[CH2:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH3:28])[CH2:22]2)=[CH:17][CH:16]=1)(=[O:12])=[O:13]

Participants

4

Reactant 1

HCID 536286362-Fluoro-4-isopropenyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 16752625HCID 16752625, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.161 g of 2-fluoro-4-isopropenyl-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.37 mmol) were dissolved in 20 ml methanol, a tip of a spatula 10% Pd/C added, and the reaction mixture hydrogenated for 3 h at 50° C. The reaction mixture was filtered over celite, washed with methanol, and the filtrate evaporated to dryness under reduced pressure. The residue was purified via silica gel chromatography on a chromabond column with ethyl acetate and ethyl acetate/methanol (10%). Fractions containing the product were combined, the solvent evaporated to yield 0.11 g of the title product.

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washwashed with methanol
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customThe residue was purified via silica gel chromatography on a chromabond column with ethyl acetate and ethyl acetate/methanol (10%)
  5. additionFractions containing the product
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-fab5c8c195c04babac518c1d83b5e5e3
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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