Potassium Fluoride → N-(2,4-dimethylphenyl)-N-isobutyl-4-(pyridine-4-ylmethoxy)benzenesulfonamide

HRID 1746404Notes

Reaction equation

HRID 1746404 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[F-].[K+].Br[CH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>C(#N)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 522689Potassium Fluoride3×HCID 6427994-(Bromomethyl)pyridineHCID 71543523N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide

Product 1

HCID 71543524N-(2,4-dimethylphenyl)-N-isobutyl-4-(pyridine-4-ylmethoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of N-(2,4-dimethylphenyl)-4-hydroxy-N-isobutylbenzenesulfonamide (33 mg, 0.099 mmol), and potassium fluoride, 40% by weight on alumina (40% KF.Al2O3 43.1 mg, 0.297 mmol) in acetonitrile (0.2 mL) were stirred for 5 mins, before addition of 4-(bromomethyl)pyridine (0.099 mmol) in acetonitrile (0.2 mL). The reaction mixture was capped and stirred at RT for 18 hours. Additional 40% KF.Al2O3 (43 mg) and more alkylating reagent (0.1 mmol) were added to the tube, which was capped and stirred for a further 18 hours. The reaction had additional potassium fluoride, 40% by weight on alumina (43 mg) and alkylating reagent (0.1 mmol), and then recapped and stirred for 2 days. The sample was filtered through cotton wool, and DMSO added to bring the total volume to 1 mL. The solutions were purified by mass directed autoprep on Sunfire C18 column using acetonitrile water with a formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product.

Workup

  1. customThe reaction mixture was capped
  2. customwas capped
  3. stirringstirred for a further 18 hours
  4. stirringstirred for 2 days
  5. filtrationThe sample was filtered through cotton wool, and DMSO
  6. additionadded
  7. customThe solutions were purified by mass
  8. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus

Sources & evidence

ORD record
ord-52d4d1f0e70d4850880fa7f4ab8688c7
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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