Sodium Hydroxide → 4-Bromo-2-methyl-1H-pyrrolo(2,3-b)pyridine

HRID 244641Notes

Reaction equation

HRID 244641 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[N:10](S(C3C=CC=CC=3)(=O)=O)[C:11]([CH3:13])=[CH:12][C:5]=12>O1CCOCC1>[Br:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][C:11]([CH3:13])=[CH:12][C:5]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 497590984-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 529877864-Bromo-2-methyl-1H-pyrrolo(2,3-b)pyridineYield 105%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

2M Sodium hydroxide solution (114 ml) was added to a solution of 4-bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (16 g) in 1,4-dioxane (320 ml) and the reaction heated at 60° C. overnight. After cooling, the aqueous layer was separated and washed with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered, and then evaporated to give title compound (10.1 g) as a cream coloured solid.

Workup

  1. temperatureAfter cooling
  2. customthe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2e5a3e18e146431f8a30721441121525
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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