Bromine → HCID 21931760, compound

HRID 1244042Notes

Reaction equation

HRID 1244042 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][CH:4]=1.[Br:16]Br>C(O)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:15])([CH3:14])[C:10](=[O:13])[N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[Br:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 21931746HCID 21931746, compound

Product 1

HCID 21931760HCID 21931760, compoundYield 567.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.14 g (0.853 mmol) 5-methoxy-1,3,3-trimethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one dissolved in 2 ml of acetic acid was added 0.136 g (0.0853 mmol) of bromine. The solution was heated to 60° C. for 1 hour. The reaction was cooled to room temperature and quenched with 5 ml of water. The pH was adjusted to 7.5 and the mixture extracted with ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4) and evaporated. The residue was chromatographed on silica using chloroform as the elutant. Appropriate fractions were combined and evaporated to yield 138 mg of 5-methoxy-6-bromo-1,3,3-trimethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one. Mass spectrum: m/e=285,287.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with 5 ml of water
  3. extractionthe mixture extracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica
  7. customevaporated

Sources & evidence

ORD record
ord-8837a8b5cef443eabd814cfca376e611
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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