Sodium hydride → 5-Chloro-6-((4'-fluoro spiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methoxy)pyridine-3-sulfonamide

HRID 1036045Notes

Reaction equation

HRID 1036045 reaction equation
[F:1][C:2]1([CH2:16][OH:17])[CH2:7][CH2:6][C:5]2([O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8]2)[CH2:4][CH2:3]1.[H-].[Na+].[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:24]=[N:25][C:26]=1Cl.[NH4+].[Cl-]>CN(C)C=O>[Cl:20][C:21]1[CH:22]=[C:23]([S:28]([NH2:31])(=[O:30])=[O:29])[CH:24]=[N:25][C:26]=1[O:17][CH2:16][C:2]1([F:1])[CH2:3][CH2:4][C:5]2([O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11]2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 67126697(4'-Fluorospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methanol

Product 1

HCID 671269175-Chloro-6-((4'-fluoro spiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-4'-yl)methoxy)pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of EXAMPLE 350C (89 mg) in N,N-dimethylformamide (3 mL) was added NaH (65% in mineral oil, 36 mg). The mixture was stirred for 30 minutes, and then 5,6-dichloropyridine-3-sulfonamide (85 mg) was added. The mixture was stirred overnight. The mixture was poured over aqueous NH4Cl and extracted with ethyl acetate (100 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. After filtration and evaporation of the solvent, the residue was loaded on a silica gel cartridge and eluted with 30% ethyl acetate in hexane to provide the title compound.

Workup

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent
  6. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f5393e1e1e4b4b0881c775b51a46e559
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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