N-Iodosuccinimide → 3-Iodo-4-methoxy-1H-pyrrolo[2,3-c]pyridine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.