N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-nitro-benzenesulfonamide → 3-Amino-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamide

HRID 25505Notes

Reaction equation

HRID 25505 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:31][CH3:32])=[C:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=3)(=[O:21])=[O:20])[CH:17]=1)=[CH:5]2>C(O)(=O)C.[Zn]>[NH2:28][C:24]1[CH:23]=[C:22]([S:19]([NH:18][C:16]2[CH:17]=[C:12]([C:6]3[NH:7][C:8]4[C:4]([CH:5]=3)=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=4)[CH:13]=[CH:14][C:15]=2[O:31][CH3:32])(=[O:20])=[O:21])[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 10298171N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-nitro-benzenesulfonamide

Product 1

HCID 102766743-Amino-N-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-benzenesulfonamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The product from Example 15 (0.388 g, 0.84 mmol) was taken up in glacial acetic acid (25 mL), and zinc dust (2.8 g, 325 mesh) was added in portions over 3 minutes and was then stirred 2 hours at room temperature. The zinc was filtered off and washed with ethyl acetate and tetrahydrofuran. The organic solution was concentrated to dryness, the residue partitioned between ethyl acetate (200 mL) and sodium bicarbonate solution (200 mL), the organic layer washed with brine and dried (magnesium sulfate), filtered, concentrated, and the resulting solid triturated with hexanes/ethyl acetate, 3/1, v/v and the insoluble portion collected by filtration to give the product as a faintly yellow solid (0.296 g), mp 235-238° C.

Workup

  1. filtrationThe zinc was filtered off
  2. washwashed with ethyl acetate and tetrahydrofuran
  3. concentrationThe organic solution was concentrated to dryness
  4. customthe residue partitioned between ethyl acetate (200 mL) and sodium bicarbonate solution (200 mL)
  5. washthe organic layer washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe resulting solid triturated with hexanes/ethyl acetate, 3/1, v/v
  10. filtrationthe insoluble portion collected by filtration

Sources & evidence

ORD record
ord-48e32bff15794902aa216c52f945f4b3
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

Loading…