HCID 10471407, compound → HCID 10381888, compound

HRID 275354Notes

Reaction equation

HRID 275354 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1>C(O)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 10471407HCID 10471407, compound

Product 1

HCID 10381888HCID 10381888, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

6-Chloro-3-(4-fluorophenyl)-1-(4-pyridyl)-lH-indole 2e (1.8 g) was dissolved in acetic acid (100 ml) and PtO2 (0.2 g) was added. After hydrogenation for 30 h at 3 ato the catalyst was filtered off, the acetic acid was evaporated in vacuo and water (50 ml) was added. The acidic solution was made alkaline (pH>9) with concentrated sodium hydroxide and extracted with ethyl acetate (2×50 ml). The combined organic phases were successively washed with diluted sodium hydroxide (50 ml), washed with brine, and dried (Na2SO4). Evaporation of the solvent gave 1.5 g of the title compound as an oil.

Workup

  1. filtrationAfter hydrogenation for 30 h at 3 ato the catalyst was filtered off
  2. customthe acetic acid was evaporated in vacuo and water (50 ml)
  3. additionwas added
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe combined organic phases were successively washed with diluted sodium hydroxide (50 ml)
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a7eae7849ca74017907dd78b268f0587
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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