4-Hydroxymethylpyridine → N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamide

HRID 594156Notes

Reaction equation

HRID 594156 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+]>CN(C)C=O>[CH2:28]([N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=1)[S:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:12]=1)(=[O:18])=[O:17])[CH:29]([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

Product 1

HCID 72194422N-isobutyl-N-(6-methoxypyridin-2-yl)-4-(pyridin-4-ylmethoxy)benzenesulfonamideYield 26.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridin-4-ylmethanol (20.22 mg, 0.185 mmol) and 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide (62.7 mg, 0.185 mmol) were dissolved in N,N-dimethylformamide (DMF) (3 mL) and sodium hydride (7.41 mg, 0.185 mmol, 60% wt in mineral oil) added. Reaction left to stir at room temperature, under nitrogen, for 3 hours. The reaction was then quenched by adding water (2 mL). The mixture was concentrated in vacuo and the product extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was dried by passing it through a hydrophobic frit, concentrated and then purified by mass directed autoprep (formic acid modifier), to give the title compound (21.2 mg). LCMS (2 min, formic) Rt 1.05 min, m/z (ES+) 428 (M+H).

Workup

  1. customReaction
  2. waitleft
  3. customThe reaction was then quenched
  4. additionby adding water (2 mL)
  5. concentrationThe mixture was concentrated in vacuo
  6. extractionthe product extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. custompurified by mass

Sources & evidence

ORD record
ord-be83ba92e3ba4af4a1704e5deb9d6574
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

Loading…