N-Iodosuccinimide → 4-chloro-3-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine
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]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- filtrationThe reaction mixture was then filtered
- 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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