Sodium hydride → N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

HRID 594162Notes

Reaction equation

HRID 594162 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([N:8]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[O:24]1[CH2:29][CH2:28][CH:27]([CH2:30][OH:31])[CH2:26][CH2:25]1.[H-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([N:8]([CH2:19][CH:20]([CH3:22])[CH3:21])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:31][CH2:30][CH:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 89875794N-(5-chloro-3-methylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

Product 1

HCID 72194556N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideYield 88%

Procedure

N-(5-chloro-3-methylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (200.5 mg, 0.562 mmol) was dissolved in dimethyl sulfoxide DMSO (2 mL) and to this solution was added (tetrahydro-2H-pyran-4-yl)methanol (98 mg, 0.84 mmol) and sodium hydride (33 mg, 0.84 mmol, 60% wt in mineral oil). The reaction was left to stir overnight at room temperature, under nitrogen. The reaction was concentrated under a stream of nitrogen, then the crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit and concentrated in vacuo to give the title compound (224 mg). LCMS (2 min, formic) Rt 1.42 min, m/z (ES+) 453 (M+H).

Workup

  1. waitThe reaction was left
  2. concentrationThe reaction was concentrated under a stream of nitrogen
  3. extractionthe crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c565362cbab040e89025704740aae3e9
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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