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

HRID 594152Notes

Reaction equation

HRID 594152 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:19])=[O:18].[H-].[Na+]>CS(C)=O>[Cl:9][C:10]1[CH:15]=[C:14]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:13]=[CH:12][C:11]=1[S:17]([N:20]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][N:26]=1)[CH2:21][CH:22]([CH3:23])[CH3:24])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2773573(Oxan-4-yl)methanolHCID 898760522-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

Product 1

HCID 721942782-chloro-N-(3,5-dimethylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 4-(hydroxylmethyl)tetrahydro-2H-pyran (2.63 mg, 0.023 mmol) and 2-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide (8.4 mg, 0.023 mmol) in dimethyl sulfoxide (200 μL) at room temperature was added sodium hydride (60% wt in mineral oil) (0.906 mg, 0.023 mmol) and the reaction stirred for 2 hours. The reaction was quenched with methanol (2 mL) and water (2 mL), then the solvents evaporated in vacuo. The crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient) to give the title compound (5.2 mg). LCMS (2 min, High pH) Rt 1.48 min, m/z (ES+) 468 (M+H).

Workup

  1. customThe reaction was quenched with methanol (2 mL) and water (2 mL)
  2. customthe solvents evaporated in vacuo
  3. customThe crude product was purified by flash silica (Si) chromatography (25% ethyl acetate-cyclohexane gradient)

Sources & evidence

ORD record
ord-623da59365e54c6c893e14d6e6078a64
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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