1,4-Dioxane → 2-(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone

HRID 1964992Notes

Reaction equation

HRID 1964992 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[O:19]1CCOCC1>[OH-].[K+]>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[CH:13]=[CH:18][CH:17]=[CH:16][C:15]=3[CH:14]=[O:19])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 150138931-Benzoyl-6-bromo-7-azaindole

Product 1

HCID 866231352-(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

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-7a4c0160a7fe4f3a97372dbf5eb815a2
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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