N-Iodosuccinimide → 4-chloro-3-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 330998Notes

Reaction equation

HRID 330998 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.C1C(=O)N([I:19])C(=O)C1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[NH:9][CH:10]=[C:11]([I:19])[C:3]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 247295844-Chloro-6-methyl-1h-pyrrolo[2,3-b]pyridine

Product 1

HCID 710904044-chloro-3-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridineYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-chloro-6-methyl-1H-pyrrolo[2,3-b]pyridine (4.06 g, 24.37 mmol) in DCM (80 mL) at 0° C., was added NIS (6.22 g, 27.6 mmol). The reaction mixture was then warmed to RT and stirred for 18 hours. The reaction mixture was then filtered (washed with excess DCM) to give the title compound (4.01 g). LCMS (A): m/z (M+H)+ 293, C8H6ClIN2 requires 292 (acidic).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. wash(washed with excess DCM)

Sources & evidence

ORD record
ord-d8ccce7840bd454ba996e1985f2eb47a
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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