Pyridine → [5-(4-Isopropyl-piperazine-1-carbonyl)-1-(3-trifluoromethyl-phenyl)-1H-indol-2-yl]-(4-methoxy-piperidin-1-yl)-methanone

HRID 1820514Notes

Reaction equation

HRID 1820514 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][CH3:30])[CH2:25][CH2:24]2)=[O:22])=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:32]([F:43])([F:42])[F:31])[CH:38]=2)[C:16]([C:21]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][CH3:30])[CH2:25][CH2:24]2)=[O:22])=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 68683427[5-(4-Isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methoxy-piperidin-1-yl)-methanone

Product 1

HCID 68681141[5-(4-Isopropyl-piperazine-1-carbonyl)-1-(3-trifluoromethyl-phenyl)-1H-indol-2-yl]-(4-methoxy-piperidin-1-yl)-methanoneYield 65%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized in analogy to example 66, from [5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4-methoxy-piperidin-1-yl)-methanone (example 21), 3-(trifluoromethyl)phenylboronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a colorless foam (65%).

Sources & evidence

ORD record
ord-a66ec98cebaf423f8940d708a9470ab3
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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