Benzenesulfonyl chloride → 1H-Pyrrolo[2,3-B]pyridine, 5-methoxy-1-(phenylsulfonyl)-
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:14]1([S:20]([N:9]2[C:6]3=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[CH:11]=[CH:10]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tetrabutylammonium bromide (1.05 g, 3.24 mmol) and 5-methoxy-1H-pyrrolo[2,3-b]pyridine (16 g, 108.1 mmol) in dichloromethane (300 mL) at 0° C. was added powdered sodium hydroxide (13 g, 324.3 mmol). The mixture was then stirred at 0° C. for 5 min. Then benzene sulfonyl chloride (18 mL, 140.54 mmol) was added to the above mixture slowly and the resulting mixture was stirred at 0° C. for 15 min before it was warmed to room temperature and stirred for 12 h. The mixture was filtered and the filtrate concentrated in vacuo and then washed with hexane to afford 1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridine (28.8 g, 93%) as a white solid: LC/MS m/e calcd for C14H12N2O3S [M+H]+ 289.33, observed 289.0.
Workup
- stirringthe resulting mixture was stirred at 0° C. for 15 min before it
- temperaturewas warmed to room temperature
- stirringstirred for 12 h
- filtrationThe mixture was filtered
- concentrationthe filtrate concentrated in vacuo
- washwashed with hexane
Sources & evidence
- ORD record
- ord-52d948b12a134e2f9c9db3b9c2efb2cd
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222416B2
Reaction notes
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