Acetic Acid → HCID 20761750, compound

HRID 1839633Notes

Reaction equation

HRID 1839633 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[CH:14][NH:15]3)[CH:6]=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>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][C:14](=[O:23])[NH:15]3)[CH:6]=1

Participants

8

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 20761749HCID 20761749, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 20761750HCID 20761750, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To the suspension of [3-(1H-indol-4-yl)-phenyl]-acetic acid methyl ester (3.72 g, 14 mmol) in t-BuOH:ethanol:acetic acid (93 mL:56 mL:67.2 mL) was added pyridinium tribromide (14.14 g, 44 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (60 mL). Water (2 mL) and zinc dust (14 g, excess) was added to the reaction mixture portionwise. After stirring at rt for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with diluted with water (380 mL), extracted with ethyl acetate, washed with 0.5 N HCl (2×), 10% Na2CO3, (2×), brine (2×), water (1×), dried over Na2SO4, concentrated and triturated with ether to give [3-(2-oxo-2,3-dihydro-1H-indol-4-yl)-phenyl]-acetic acid methyl ester.

Workup

  1. stirringAfter stirring at rt 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
  5. additionwith diluted with water (380 mL)
  6. extractionextracted with ethyl acetate
  7. washwashed with 0.5 N HCl (2×), 10% Na2CO3, (2×), brine (2×), water (1×)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customtriturated with ether

Sources & evidence

ORD record
ord-1a51c661c8eb40de8a3d0de2aae06d06
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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