2-(p-Toluenesulfonyl)-5-tributylstannylisoindoline → Ethyl 8-chloro-1-cyclopropyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 377286Notes

Reaction equation

HRID 377286 reaction equation
Br[C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]2[CH:13]2[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.[C:22]1([CH3:53])[CH:27]=[CH:26][C:25]([S:28]([N:31]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[C:36]([Sn](CCCC)(CCCC)CCCC)[CH:37]=3)[CH2:32]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1>>[Cl:12][C:11]1[C:2]([C:35]2[CH:34]=[C:33]3[C:38](=[CH:37][CH:36]=2)[CH2:39][N:31]([S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:53])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[CH2:32]3)=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]2=[O:21]

Participants

3

Reactant 2

HCID 158708542-(p-Toluenesulfonyl)-5-tributylstannylisoindolineHCID 193583443-Quinolinecarboxylic acid,7-bromo-8-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-,ethyl ester

Product 1

HCID 19358313Ethyl 8-chloro-1-cyclopropyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 79%

Procedure

In the same manner as in Example 1, 0.45 g of ethyl 7-bromo-8-chloro-1-cyclopropyl-1,4-dihydro-4-oxoquinoline-3-carboxylate was reacted with 1.02 g of 2-(p-toluenesulfonyl)-5-tributylstannylisoindoline to obtain 0.54 g of ethyl 8-chloro-1-cyclopropyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Sources & evidence

ORD record
ord-0eda879b9abe427ba02e358f891c7637
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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