N-Iodosuccinimide → 3-iodo-4-nitro-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:10][CH:11]=[CH:12][C:5]=12)([O-:3])=[O:2].C1C(=O)N([I:20])C(=O)C1>C(Cl)Cl>[I:20][C:12]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[NH:10][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 4-nitro-1H-pyrrolo[2,3-b]pyridine (4.5 g, 27.6 mmol) in DCM (180 mL) was added NIS (6.83 g, 30.3 mmol) over 30 mins at 0° C. The resulting mixture was stirred at 0° C. for another 1 hour. The reaction mixture was concentrated. The residue was suspended in DCM (ca. 25 mL), the solid was filtered and dried in a vacuum oven to give the title compound (8.51 g). LCMS (A): m/z (M+H)+ 290, C7H4IN3O2 requires 289 (acidic).
Workup
- concentrationThe reaction mixture was concentrated
- filtrationthe solid was filtered
- customdried in a vacuum oven
Sources & evidence
- ORD record
- ord-8fe97226204746689d50f3d53256a259
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877742B2
Reaction notes
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