HCID 57742989, compound → HCID 57742997, compound

HRID 1924240Notes

Reaction equation

HRID 1924240 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]([CH2:12][C:13]2[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=2)[C:3]1=[O:20]>CC(O)=O.[Zn]>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]([CH2:12][C:13]1[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:3](=[O:20])[CH2:2]2

Participants

4

Reactant 1

HCID 57742989HCID 57742989, compound

Product 1

HCID 57742997HCID 57742997, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

In a 50 ml, three-necked flask fitted with a magnetic stirrer under inert atmosphere, 3,3-dibromo-5-chloro-1-[(2-fluoropyridin-3-yl)methyl]-1,3-dihydro-2H-indol-2-one x73 (1.79 g, 4.12 mmol) is dissolved in AcOH (20 ml) and, at 0° C., powdered zinc (2.7 g, 41.2 mmol) is added. The mixture is stirred for 10 min at room temperature, filtered on Celite and concentrated to dryness. The residue is purified by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v)) to give 104 mg of 5-chloro-1-[(2-fluoropyridin-3-yl)methyl]-1,3-dihydro-2H-indol-2-one 227.

Workup

  1. filtrationfiltered on Celite
  2. concentrationconcentrated to dryness
  3. customThe residue is purified by chromatography on silicagel (Hexane/AcOEt:6/4 (v/v))

Sources & evidence

ORD record
ord-a117732158034d1994c07c317b4218ea
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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