Sodium Dithionite → HCID 131732287, compound

HRID 1424828Notes

Reaction equation

HRID 1424828 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[C:9]([C:11]1[CH:12]=[C:13]([N:20]([C:25]2[C:44]([CH:45]3[CH2:47][CH2:46]3)=[CH:43][C:28]3[C:29]([C:39]([NH:41][CH3:42])=[O:40])=[C:30]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[O:31][C:27]=3[CH:26]=2)[S:21]([CH3:24])(=[O:23])=[O:22])[CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)#[N:10]>O.C1COCC1>[NH2:17][C:16]1[CH:15]=[CH:14][C:13]([N:20]([C:25]2[C:44]([CH:45]3[CH2:47][CH2:46]3)=[CH:43][C:28]3[C:29]([C:39]([NH:41][CH3:42])=[O:40])=[C:30]([C:32]4[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=4)[O:31][C:27]=3[CH:26]=2)[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:12][C:11]=1[C:9]#[N:10]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 131732286HCID 131732286, compound

Product 1

HCID 131732287HCID 131732287, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Na2S2O4 (7.24 g, 41.6 mmol) in water (70 mL) was added dropwise to a solution of 6-(N-(3-cyano-4-nitrophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (3.8 g, 6.93 mmol) in THF at room temperature under N2. The mixture was stirred overnight. H2O was added to the mixture and then extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4. After concentration, the crude residue was purified by chromatography on silica gel eluted with 0-20% EtOAC in DCM to give the desired product as a white solid (2.67 g, 74.3%). LCMS (m/z, ES+)=519 (M+H+)

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe crude residue was purified by chromatography on silica gel
  6. washeluted with 0-20% EtOAC in DCM

Sources & evidence

ORD record
ord-9adfd622c4684c3bbe919994721e6270
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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