p-Toluenesulfonic acid monohydrate → HCID 59257843, compound

HRID 1094093Notes

Reaction equation

HRID 1094093 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:17][C:18]([O:20]CC)=O)=[CH:5][N:6]2[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:20]=[C:18]1[CH2:17][C:4]2=[CH:5][N:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]3[C:3]2=[C:2]([CH:10]=[CH:9][CH:8]=3)[NH:1]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 66636677HCID 66636677, compound

Product 1

HCID 59257843HCID 59257843, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of diethyl 2,2′-(4-amino-1H-indole-1,3-diyl)diacetate from Step F (83 mg, 0.273 mmol) in toluene (8 mL) was added p-toluenesulfonic acid monohydrate (5 mg, 0.026 mmol) and the mixture was heated at reflux. After 2 h, the reaction was allowed to cool to ambient temperature and the mixture was partitioned between EtOAc (40 mL) and aqueous NaHCO3 (15 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 92:8, to give the title compound. MS: m/z=259 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customthe mixture was partitioned between EtOAc (40 mL) and aqueous NaHCO3 (15 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-92b2aaacad6d4cb0adad2465e68c790c
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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