Acetic Acid → HCID 22561683, compound

HRID 1839622Notes

Reaction equation

HRID 1839622 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH:13]=[CH:14][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:23])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn].O>[CH3:20][N:18]([CH3:19])[CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C:2](=[O:23])[NH:1]3)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 22561922HCID 22561922, compound

Product 1

HCID 22561683HCID 22561683, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To the suspension of {2-[3-(1H-indol-4-yl)-phenyl]-ethyl}-dimethyl-amine (600 mg, 2.2 mmol) in t-BuOH:ethanol:acetic acid (14.5 mL:8.8 mL:10.5 mL) was added pyridinium tribromide (2.3 g, 6.6 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (9.24 mL). Water (0.32 mL) and zinc dust (2.2 g, 61.2 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (3×), sat. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was dissolved in methanol (10 mL) and hydrogenated using 10% Pd—C for overnight. The reaction was filtered through celite and the filtrate was concentrated. The residue was purified on a silica gel column to give 4-[3-(2-dimethylamino-ethyl)-phenyl]-1,3-dihydro-indol-2-one

Workup

  1. stirringAfter stirring for one hour
  2. filtrationany unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (3×), sat. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in methanol (10 mL)
  9. customfor overnight
  10. filtrationThe reaction was filtered through celite
  11. concentrationthe filtrate was concentrated
  12. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-1324ce441f3348548512fbb58264a3e1
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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