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 1N 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-ca545b8c34dc419e874d032e95aa6102
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825212B2
Reaction notes
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