Indole → 1-(Phenylsulfonyl)-1H-indole

HRID 1871904Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([S:16]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 798Indole

HCID 7369Benzenesulfonyl chloride

Product 1

HCID 3150171-(Phenylsulfonyl)-1H-indole

Procedure

An appropriate indole is N-deprotonated and the resulting anion reacted with phenylsulfonyl chloride to provide the corresponding 1-phenylsulfonylindole. This protected indole may be purified or treated directly with an appropriate base, typically a lithium amide such as lithium diisopropylamide, and then reacted with an appropriate tropanone to provide the corresponding 3-hydroxy-3-(1-phenylsulfonylindol-2-yl)-8-azabicyclo[3.2.1]oct-2-ane.

Sources & evidence

ORD record: ord-00390963bdf54865a0665bb5534b4c83
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107307

Reaction notes

Loading…