Methanol → N-(2,4-dimethylphenyl)-N-isobutyl-4-((pyridin-4-yloxy)methyl)benzenesulfonamide

HRID 1746407Notes

Reaction equation

HRID 1746407 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[CH3:24])[CH2:13][CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:27][OH:28]>CC1CCCO1>[CH3:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:28][C:27]2[CH:18]=[CH:17][N:12]=[CH:13][CH:14]=2)=[CH:4][CH:5]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 867315854-(bromomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide

Product 1

HCID 71543613N-(2,4-dimethylphenyl)-N-isobutyl-4-((pyridin-4-yloxy)methyl)benzenesulfonamideYield 10%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

To a solution of an alcohol (1.276 mg, 0.075 mmol, see Table 4 for specific alcohol used for each reaction) and 4-(bromomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (0.031 g, 0.075 mmol) in 2-Methyltetrahydrofuran (2-MeTHF) (1 mL) stirred under nitrogen at room temperature was added solid sodium hydride (1.800 mg, 0.075 mmol) (tip of spatula). The reaction mixture was stirred at 20° C. for 3 hrs. The reaction was carefully quenched with water (5 drops per reaction). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. The sample was dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoprep on an Xbridge column using acetonitrile:water with an ammonium carbonate modifier. The solvent was dried under a stream of nitrogen in the Radley's blowdown apparatus to give the required product (3.89 mg, 10% yield).

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 3 hrs
  2. customThe reaction was carefully quenched with water (5 drops per reaction)
  3. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  4. customto give the crude product
  5. customDMSO 1 mL and purified by mass
  6. customThe solvent was dried under a stream of nitrogen in the Radley's blowdown apparatus

Sources & evidence

ORD record
ord-8e1e328ae26948e6bd3209fdc4cd0685
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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