N-Iodosuccinimide → 4-bromo-3-iodo-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 331010Notes

Reaction equation

HRID 331010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[CH:10][C:3]=12.C1C(=O)N([I:19])C(=O)C1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[C:10]([I:19])[C:3]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 529877864-Bromo-2-methyl-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 710901934-bromo-3-iodo-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (D24) (1.65 g, 7.82 mmol) in DCM (70 mL) was added NIS (1.935 g, 8.60 mmol) at 0° C. and the mixture was stirred for 1.5 hour at 0° C. The mixture was evaporated in vacuo. DCM (ca. 20 mL) was added to the residue. The formed precipitate was filtered, rinsed with DCM to give the title compound (2.45 g). LCMS (A): m/z (M+H)+ 337/339, C8H6BrIN2 requires 336/338 (acidic).

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionDCM (ca. 20 mL) was added to the residue
  3. filtrationThe formed precipitate was filtered
  4. washrinsed with DCM

Sources & evidence

ORD record
ord-864ac5436dfa4d54a94e5208c668edf3
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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