Morpholine → Ethyl 5-chloro3-(thiomorpholin-4-ylsulfonyl)-1H-indole-2-carboxylate

HRID 227471Notes

Reaction equation

BrC1C=[C:4]2[C:8](=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)[C:6](C(OCC)=O)=[C:5]2[S:25](Cl)(=O)=O.[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[N:35](S(C1C=CC=CC=1)(=O)=O)[C:34]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:33]2[S:53](Cl)(=[O:55])=[O:54].N1CCOCC1.N1CCSCC1>>[Cl:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:33]2[S:53]([N:7]1[CH2:6][CH2:5][S:25][CH2:4][CH2:8]1)(=[O:54])=[O:55]

Participants

Reactant 4

HCID 8083Morpholine

HCID 67164Thiomorpholine

HCID 22401482ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate

HCID 86592455ethyl 3-(chlorosulfonyl)-5-bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 68445271Ethyl 5-chloro3-(thiomorpholin-4-ylsulfonyl)-1H-indole-2-carboxylate

Procedure

The titled compound was prepared using the procedures described in Steps B and C of Example 2, replacing in Step B ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 5-chloro-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate, and morpholine with thiomorpholine. Proton NMR for the product was consistent with the titled compound. ESI+MS: 389.1 [M+H]+.

Workup

customThe titled compound was prepared

Sources & evidence

ORD record: ord-f9debcf76fd946b6b1492ae50d7ecd09
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560546B2

Reaction notes

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