p-Toluenesulfonic acid monohydrate → HCID 59257843, compound

HRID 1696354Notes

Reaction equation

HRID 1696354 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-958da05c713645b586a5594096e8691c
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

Loading…