Sodium Dithionite → HCID 131732307, compound

HRID 2272356Notes

Reaction equation

HRID 2272356 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]3[CH:28]=[C:27]([N:29]([C:34]4[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[C:36]([C:43]#[N:44])[CH:35]=4)[S:30]([CH3:33])(=[O:32])=[O:31])[C:26]([CH:45]4[CH2:47][CH2:46]4)=[CH:25][C:19]=3[C:20]=2[C:21]([NH:23][CH3:24])=[O:22])=[CH:12][CH:11]=1>O.C1COCC1>[NH2:40][C:37]1[CH:38]=[CH:39][C:34]([N:29]([C:27]2[C:26]([CH:45]3[CH2:47][CH2:46]3)=[CH:25][C:19]3[C:20]([C:21]([NH:23][CH3:24])=[O:22])=[C:16]([C:13]4[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=4)[O:17][C:18]=3[CH:28]=2)[S:30]([CH3:33])(=[O:32])=[O:31])=[CH:35][C:36]=1[C:43]#[N:44]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 131732306HCID 131732306, compound

Product 1

HCID 131732307HCID 131732307, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Na2S2O4 (4.98 g, 28.6 mmol) in water (50 mL) was added dropwise to a solution of 2-(4-chlorophenyl)-6-(N-(3-cyano-4-nitrophenyl)methylsulfonamido)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide (2.70 g, 4.77 mmol) in THF at room temperature under N2. The mixture was stirred overnight. More water was added and then extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4. Concentrated under reduced pressure, the crude residue was purified by chromatography on silica gel eluted with 0-15% EtOAc in DCM to give the product (2.3 g, 83%) as a white solid. LCMS (m/z, ES+)=535 (M+H+).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationConcentrated under reduced pressure
  5. customthe crude residue was purified by chromatography on silica gel
  6. washeluted with 0-15% EtOAc in DCM

Sources & evidence

ORD record
ord-4496337c3d3a42adaa9f6d4a6dbadd7a
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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