Potassium Carbonate → 4-(3-methanesulfonyl-propoxy)-1H-indole
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6].[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:18])[C:12]=2[CH:11]=[CH:10]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:8][S:5]([CH2:4][CH2:3][CH2:2][O:18][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[CH:10][NH:9]2)(=[O:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1-Chloro-3-(methanesulfonyl)-propane (160 g) was added to 1H-indol-4-ol (108.77 g) in 1 L MeCN, and 338 g K2CO3 and 13.36 g KI were added. The reaction mixture was stirred overnight at 80° C., then cooled and filtered through celite. The filtrate was vacuum distilled and solvent replaced with DCM (700 mL). The mixture was filtered, and the solvent removed in vacuo and replaced with MeOH (600 mL). The solvent was partially removed in vacuo at 40° C. and crystallization occurred. After cooling, additional MeOH was added and the slurry was filtered. The collected solid was rinsed with cold MeOH and dried overnight at 35° C. in vacuo under N2 to provide 4-(3-methanesulfonyl-propoxy)-1H-indole (82%).
Workup
- additionwere added
- temperaturecooled
- filtrationfiltered through celite
- distillationdistilled
- filtrationThe mixture was filtered
- customthe solvent removed in vacuo
- customThe solvent was partially removed in vacuo at 40° C.
- customcrystallization
- temperatureAfter cooling
- additionadditional MeOH was added
- filtrationthe slurry was filtered
- washThe collected solid was rinsed with cold MeOH
- customdried overnight at 35° C. in vacuo under N2
Sources & evidence
- ORD record
- ord-4bf94e4e6d854a239679405189ab15b4
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642601B2
Reaction notes
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