1H-Pyrrolo(2,3-b)pyridine → 3-Bromo-1H-pyrrolo[2,3-b]pyridine

HRID 1820874Notes

Reaction equation

HRID 1820874 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Br:10]N1C(=O)CCC1=O.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1.O>[Br:10][C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 61475Sodium Thiosulfate PentahydrateHCID 67184N-bromobutanimide

Product 1

HCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7-Azaindole (2, 3.57 g, 30.2 mmol) was dissolved in tetrahydrofuran (240 mL) under an atmosphere of nitrogen. At −40° C., N-bromosuccinimide (5.38 g, 30.2 mmol) in tetrahydrofuran was added under an atmosphere of nitrogen. The reaction mixture was stirred for a few hours as it was gradually warmed to room temperature and the reaction was followed by TLC. The reaction was quenched with sodium thiosulfate pentahydrate (7.50 g, 30.2 mmol) in water (1M). Two layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried with anhydrous sodium sulfate, and evaporated to dryness. The crude material was purified by column chromatography (25-40% ethyl acetate in hexanes) to yield the desired product as a white solid, 3, (4.20 g, 21.3 mmol). MS(ESI) [M+H+]+=198.5.

Workup

  1. customTwo layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe crude material was purified by column chromatography (25-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bd0c3e19c9b1437d9888842b01d52c24
Source dataset
uspto-grants-2009_10
Patent number
US07605168B2

Reaction notes

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