1-Benzoyl-6-bromo-7-azaindole → 6-Bromo-7-azaindole

HRID 250688Notes

Reaction equation

HRID 250688 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8](C(C3C=CC=CC=3)=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1>O1CCOCC1.[OH-].[K+]>[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 150138931-Benzoyl-6-bromo-7-azaindole

Product 1

HCID 111599156-Bromo-7-azaindole

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone, 586 was dissolved in 20 mL of dioxane and 20 mL of 2M KOH (aq). This was stirred at ambient temperature until analysis indicated all of the starting material had been consumed (2 to 4 hours). The reaction was diluted with 50 mL of ethyl acetate and washed with 2×25 mL of NaHCO3 (aq. satd.) and 25 mL of brine. The organic layer was dried with sodium sulfate, evaporated and purified by column chromatography. Combined steps 2 and 3 gave approximately 65% overall yield.

Workup

  1. customhad been consumed (2 to 4 hours)
  2. additionThe reaction was diluted with 50 mL of ethyl acetate
  3. washwashed with 2×25 mL of NaHCO3 (aq. satd.) and 25 mL of brine
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customevaporated
  6. custompurified by column chromatography
  7. customgave approximately 65% overall yield

Sources & evidence

ORD record
ord-468932b945504d98849e04ff8f3aaa0c
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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