Water → 3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1024410Notes

Reaction equation

HRID 1024410 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.O>C(Cl)(Cl)Cl>[Br:1][C:12]1[C:6]2[C:7](=[N:8][CH:9]=[C:4]([Cl:3])[CH:5]=2)[NH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 272827223-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridineYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of bromine (3.5 ml) in chloroform (40 ml) was added dropwise to an ice-cold solution of the 5-chloro-1H-pyrrolo[2,3-b]pyridine (3) (10 g, 65 mM) in chloroform (260 ml). The reaction mixture was stirred for 60 minutes at 0° C. The reaction mixture was then hydrolysed with water and the pH of the solution was adjusted to 10. The resulting solid was removed by filtration, and the. aqueous was extracted with dichloromethane. The organic was washed with water, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (10.5 g, 69%). 1H NMR (DMSO-d6) 7.8 (1H,$), 7.9 (1H, s), 8.3 (1H, s)

Workup

  1. customThe resulting solid was removed by filtration
  2. extractionaqueous was extracted with dichloromethane
  3. washThe organic was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37590ccca7684865ac46aba9d29ac162
Source dataset
uspto-grants-2014_05
Patent number
US08722889B2

Reaction notes

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