Acetic Acid → 2h-Pyrrolo[2,3-b]pyridin-2-one,5-benzoyl-1,3-dihydro-1-methyl-

HRID 53174Notes

Reaction equation

HRID 53174 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]2[C:16](Br)(Br)[C:15](=[O:19])[N:14]([CH3:20])[C:11]2=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:23])C>[Zn]>[C:1]([C:8]1[CH:9]=[C:10]2[CH2:16][C:15](=[O:19])[N:14]([CH3:20])[C:11]2=[N:12][CH:13]=1)(=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 190792845-benzyl-3,3-dibromo-1-methyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 105387522h-Pyrrolo[2,3-b]pyridin-2-one,5-benzoyl-1,3-dihydro-1-methyl-Yield 60%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Add a spatula tip of zinc to a solution of 40 mg of the compound of Step 2 in acetic acid. After 30 minutes' stirring, concentrate to dryness under reduced pressure, take up in water and extract with dichloromethane. The crude product obtained by concentrating to dryness is purified by chromatography on a silica column (eluant: petroleum ether/ethyl acetate, 6/4). The title product is obtained in the form of an oil in a yield of 60%. ##STR63##

Workup

  1. concentrationconcentrate to dryness under reduced pressure
  2. extractionextract with dichloromethane
  3. customThe crude product obtained
  4. concentrationby concentrating to dryness
  5. customis purified by chromatography on a silica column (eluant: petroleum ether/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-9d8694f74ab1450890e4ae2d1d8faf8c
Source dataset
uspto-grants-1997_04
Patent number
US05618819

Reaction notes

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