Sodium Hydroxide → 3-bromo-1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1622886Notes

Reaction equation

HRID 1622886 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([F:12])=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1)[CH3:2].[OH-].[Na+].[Br:15]N1C(=O)CCC1=O>CN(C=O)C>[Br:15][C:5]1[C:6]2[C:7](=[N:8][C:9]([F:12])=[CH:10][CH:11]=2)[N:3]([CH2:1][CH3:2])[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 678163901-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 678143683-bromo-1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridineYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-ethyl-6-fluoro-1H-pyrrolo[2,3-b]pyridine (16.38 g, 99.77 mmol) in DMF (300 mL) is cooled to 15° C. with stirring. To this is added sodium hydroxide (4.39 g, 109.7 mmol), followed by N-bromosuccinimide (19.53 g, 109.7 mmol) portionwise over 5 minutes, and then the reaction is allowed to stir at room temperature overnight. The reaction is poured onto brine (ca. 500 mL) and the product extracted with CHCl3 (ca. 2×300 mL). The combined organic phase is dried over magnesium sulphate, filtered, and concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 60% DCM in hexane, to give the title compound as a light yellow oil (23.4 g, 96.4 mmol). MS (m/z): 243/245 (M+1).

Workup

  1. stirringto stir at room temperature overnight
  2. additionThe reaction is poured onto brine (ca. 500 mL)
  3. extractionthe product extracted with CHCl3 (ca. 2×300 mL)
  4. dry with materialThe combined organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a brown oil
  8. customThis is purified by column chromatography on silica
  9. washeluting with 0 to 60% DCM in hexane

Sources & evidence

ORD record
ord-c26db0c0d9954cfe85b61dcbe5874ec0
Source dataset
uspto-grants-2014_07
Patent number
US08778946B2

Reaction notes

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