Methyl iodide → 6-Bromo-1,3-dimethyl-1H-indole
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:11])=[CH:7][N:8]2[CH3:14])=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-bromo-3-methyl-1H-indole (200 mg, 0.95 mmol) in DMF (8 mL) was added NaH (114 mg, 2.85 mmol, m %/60%). The mixture was stirred at room temperature for 1 h before the addition of MeI (162 mg, 1.14 mmol). The system was stirred at room temperature for 4 h then the mixture was quenched with water and extracted with EtOAc. The organic layer was concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 224.1 [M+H]+.
Workup
- customthe mixture was quenched with water
- extractionextracted with EtOAc
- concentrationThe organic layer was concentrated
- customto give crude product which
- customwas used in next step without further purification
Sources & evidence
- ORD record
- ord-46c41d0d9f384c2984f02f3473799030
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906900B2
Reaction notes
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