N-Iodosuccinimide → 5-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1693693Notes

Reaction equation

HRID 1693693 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[I:12]N1C(=O)CCC1=O>CC(C)=O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]2[C:10]([I:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 569657275-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 96%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
23 °C

Procedure

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (5.19 g, 22.4 mmol) and N-iodosuccinimide (5.55 g, 24.6 mmol) were suspended in 100 mL acetone. The mixture was stirred at 23° C. for 2 h and diluted with 150 mL water and 20 mL of saturated sodium thiosulfate solution. The precipitate was filtered and residual water was removed by dissolving the solids in dry benzene and followed by evaporation (2×100 mL) to yield 5-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (7.68 g, 21.5 mmol, 96%). 1H NMR (500 MHz, DMSO-d6) δ 12.65 (bs, 1H), 8.45 (s, 1H), 7.87 (d, J=3 Hz, 1H). MS: m/z 356.8/358.8 (M+H+).

Workup

  1. filtrationThe precipitate was filtered
  2. customresidual water was removed
  3. dissolutionby dissolving the solids in dry benzene
  4. customfollowed by evaporation (2×100 mL)

Sources & evidence

ORD record
ord-ff3ed8518a87496f9d40957e971e0961
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…