N-Iodosuccinimide → 3-Iodo-4-methoxy-1H-pyrrolo[2,3-c]pyridine

HRID 1747276Notes

Reaction equation

HRID 1747276 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[N:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C1C(=O)N([I:19])C(=O)C1>C(Cl)(Cl)Cl>[I:19][C:5]1[C:4]2[C:8](=[CH:9][N:10]=[CH:11][C:3]=2[O:2][CH3:1])[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 224762374-Methoxy-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 894455493-Iodo-4-methoxy-1H-pyrrolo[2,3-c]pyridineYield 91.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Methoxy-6-azaindole (662 mg, 4.47 mmol) was dissolved in CHCl3 (20 mL), NIS (1.06 g, 4.69 mmol) was added and the reaction mixture was stirred for 18 h. The precipitate was collected by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (50 mL), washed with 10% aq sodium thiosulfate (50 mL), sat aq NaHCO3 (50 mL) and water (50 mL), dried (MgSO4), concentrated in vacuo and combined with the precipitate to give the title compound as a red solid (1.12 g, 91%). LCMS (ES+): 274.9 [MH]+. HPLC: Rf 3.98 min, 96% purity.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 mL)
  4. washwashed with 10% aq sodium thiosulfate (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54f81f6a0ec4411bab7a9bdae1e4d137
Source dataset
uspto-grants-2015_10
Patent number
US09150574B2

Reaction notes

Loading…