Bromine → HCID 19079294, compound

HRID 53167Notes

Reaction equation

HRID 53167 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:8]2=[N:9][CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[CH:12]=[C:7]2[CH2:6][C:5]1=[O:16]>C(O)(=O)C>[Br:1][CH2:14][C:13]([C:11]1[CH:12]=[C:7]2[CH2:6][C:5](=[O:16])[N:4]([CH3:3])[C:8]2=[N:9][CH:10]=1)=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 108453511,3-dihydro-1-methyl-5-acetyl-2H-pyrrolo[2,3-b]pyridin-2-one

Product 1

HCID 19079294HCID 19079294, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

Add 170 mg (1.05 mmol) of bromine dissolved in 1 ml of acetic acid dropwise to a solution of 200 mg (1.05 mmol) of 1,3-dihydro-1-methyl-5-acetyl-2H-pyrrolo[2,3-b]pyridin-2-one (obtained as described in Example 13 hereinafter) in 4 ml of acetic acid. After 6 hours' heating at 80° C., the acetic acid is removed under reduced pressure and the residue is taken up in water and then extracted with dichloromethane. The crude product obtained is purified by chromatography on silica gel (eluant ethyl acetate/petroleum ether/dichloromethane, 1/1/1). Yield: 60%. ##STR43##

Workup

  1. customthe acetic acid is removed under reduced pressure
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-18bc507725574e34931fd50b8d965b26
Source dataset
uspto-grants-1997_04
Patent number
US05618819

Reaction notes

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