Acetic Acid → HCID 22561931, compound

HRID 1839630Notes

Reaction equation

HRID 1839630 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.C([OH:14])C.C(O)(=O)C.[Br-:19].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[Br:19][C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:14])[NH:8]2

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 138725-MethoxyindoleHCID 21124087Pyridiniumtribromide

Product 1

HCID 22561931HCID 22561931, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 5-methoxyindole (5.0 g, 34 mmol) in t-BuOH:ethanol:acetic acid (215 mL:127 mL:66 mL) was added pyridinium tribromide (32.6 g, 102 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added with more acetic acid (165 mL). Zinc dust (11.1 g, 170 mmol) was added to the reaction mixture portionwise. After stirring for one hour, the unreacted zinc was filtered off, and the solvent was removed under reduced pressure. The residue was diluted with water, extracted with ethyl acetate. The combined extracts were washed with water (5×), sat. NaHCO3 (2×), brine (3×), dried over Na2SO4, concentrated, triturated with ether to give 2.12 g (26%) of 4-bromo-5-methoxy-1,3-dihydro-indol-2-one.

Workup

  1. stirringAfter stirring for one hour
  2. filtrationthe unreacted zinc was filtered off
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with water (5×), sat. NaHCO3 (2×), brine (3×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customtriturated with ether

Sources & evidence

ORD record
ord-5c3a637e95924832843555cf26256d24
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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