HCID 57543262, compound → HCID 11665624, compound

HRID 1867571Notes

Reaction equation

HRID 1867571 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:11])[N:4]([CH2:12][C:13]([NH2:15])=[O:14])[C:3]1=[O:16]>CC(O)=O.[Zn]>[F:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:2][C:3](=[O:16])[N:4]2[CH2:12][C:13]([NH2:15])=[O:14]

Participants

4

Reactant 1

HCID 57543262HCID 57543262, compound

Product 1

HCID 11665624HCID 11665624, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (4.46 g, 0.068 mol) is added to a stirred solution of the crude 2-(3,3-dibromo-4-fluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 3 (theorical: 6.32 mmol) in AcOH (20 ml) at 0° C. After 1 hour, the reaction mixture is filtered through a Celite pad. The filtrate is diluted with AcOEt and cold water. The pH is adjusted to 7 and the layers are separated. The aqueous phase is extracted again with AcOEt. Organic layers are dried over Na2SO4 and concentrated. Several attempts to cristallize in AcOEt failed. The crude reaction mixture is purified by reverse phase HPLC (LC-MS, acetonitrile/H2O). 2-(4-fluoro-2-oxo-2,3-dihydro-1H-indol-1-yl)acetamide 9 is obtained as a white solid.

Workup

  1. filtrationthe reaction mixture is filtered through a Celite pad
  2. additionThe filtrate is diluted with AcOEt and cold water
  3. customthe layers are separated
  4. extractionThe aqueous phase is extracted again with AcOEt
  5. dry with materialOrganic layers are dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude reaction mixture
  8. customis purified by reverse phase HPLC (LC-MS, acetonitrile/H2O)

Sources & evidence

ORD record
ord-bf2d9a0b5af449ffb2efa749af57af11
Source dataset
uspto-grants-2009_12
Patent number
US07632856B2

Reaction notes

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