Iodine → 3-Iodo-7-azaindole
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[I:10]I.[I-].[K+].[OH-].[Na+]>C(O)C.O>[I:10][C:3]1[C:4]2[C:9](=[N:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of 7-azaindole (20.0 g, 169 mmol) in ethanol is treated with iodine (57.9 g, 228 mmol), potassium iodide (37.8 g, 228 mmol), and 1 N aqueous NaOH (204 mL, 204 mmol). After stirring for 4 h at 20° C., the reaction is diluted with water and extracted with ethyl acetate. The organic extracts are combined and concentrated in vacuo. The resultant residue is crystallized from methanol/water to afford the title compound as a pinkish-white solid, 35.4 g, mp 201-204° C., characterized by mass spectral and HNMR analyses.
Workup
- extractionextracted with ethyl acetate
- concentrationconcentrated in vacuo
- customThe resultant residue is crystallized from methanol/water
Sources & evidence
- ORD record
- ord-dca8cd590f40451fa651317e15e2e238
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585873B2
Reaction notes
Loading…