Sulfuryl chloride → 2-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.S(Cl)([Cl:14])(=O)=O>C(O)(=O)C>[Cl:14][C:3]1[NH:4][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-methylpyrrolo[2,3-b]pyridine (0,5 g 0.0038 mol) was treated in 2 ml acetic acid with an equimolecular amount of sulfuryl chloride at 0° C. for 5 min. The mixture was allowed to warm to room temperature and was stirred for 5 min. After evaporation the residue was dissolved in methylene chloride and was treated with bicarbonate. The organic layer was separated, dried and removed under reduced pressure. Chromatography on silica gel eluting with ethyl acetate gave the desired product. (0,18 g 29%).
Workup
- customAfter evaporation the residue
- dissolutionwas dissolved in methylene chloride
- additionwas treated with bicarbonate
- customThe organic layer was separated
- customdried
- customremoved under reduced pressure
Sources & evidence
- ORD record
- ord-51ced4447db94485886c5ff981b71509
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05439917
Reaction notes
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