HCID 59129757, compound → HCID 11276477, compound

HRID 1991473Notes

Reaction equation

HRID 1991473 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([CH:12]([CH3:16])[C:13]([NH2:15])=[O:14])[C:3]1=[O:17]>CC(O)=O.[Zn]>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH:12]([CH3:16])[C:13]([NH2:15])=[O:14])[C:3](=[O:17])[CH2:2]2

Participants

4

Reactant 1

HCID 59129757HCID 59129757, compound

Product 1

HCID 11276477HCID 11276477, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (23.71 g, 0.58 mol) was added to a stirred solution of compound 31 (theoretical: 58.4 mmol) in AcOH (110 ml) at 0° C. After 1 hour, the reaction mixture was filtered through a Celite pad. The filtrate was diluted with AcOEt and cold water. The pH was adjusted to 7 and the layers were separated. The aqueous phase was extracted again with AcOEt. Organic layers were dried over Na2SO4 and concentrated. The beige solid was cristallized in AcOEt and afforded 2-(5-chloro-2-oxo-2,3-dihydro-1H-indol-1-yl)propanamide 32 as a white solid.

Workup

  1. filtrationthe reaction mixture was filtered through a Celite pad
  2. additionThe filtrate was diluted with AcOEt and cold water
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted again with AcOEt
  5. dry with materialOrganic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb9f6ec32db34f1d8d9c7b09a4777a7e
Source dataset
uspto-grants-2010_01
Patent number
US07645887B2

Reaction notes

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