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Pyridine → [5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-(4-trifluoromethyl-phenyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone

HRID 1820426
Notes
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Reaction equation

HRID 1820426 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23]([N:25]3[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([C:38]3[CH:39]=[CH:40][C:35]([C:34]([F:45])([F:44])[F:33])=[CH:36][CH:37]=3)[C:18]([C:23]([N:25]3[CH2:30][CH2:29][S:28](=[O:31])(=[O:32])[CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 68680722[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone

Product 1

HCID 68683732[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-(4-trifluoromethyl-phenyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanoneYield 15%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst
HCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized in analogy to example 66, from [5-(4-cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone (example 34), 4-(trifluoromethyl)phenylboronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a light yellow solid (15%).

Sources & evidence

ORD record
ord-2fb9fce07355449ba49231bcdb956ba0
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601711B2

Reaction notes

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