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

HRID 707034Notes

Reaction equation

HRID 707034 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-81441dc09adb42d7a7c791d2bacfc778
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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