Pyridine → N-{4-[5-(4-Cyclobutyl-piperazine-1-carbonyl)-2-(4,4-difluoro-piperidine-1-carbonyl)-indol-1-yl]-phenyl}-methanesulfonamide

HRID 1820480Notes

Reaction equation

HRID 1820480 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([C:22]([N:24]3[CH2:29][CH2:28][C:27]([F:31])([F:30])[CH2:26][CH2:25]3)=[O:23])=[CH:16]4)=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:32][S:33]([NH:36][C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1)(=[O:35])=[O:34].N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:1]1([N:5]2[CH2:6][CH2:7][N:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([C:40]3[CH:39]=[CH:38][C:37]([NH:36][S:33]([CH3:32])(=[O:34])=[O:35])=[CH:42][CH:41]=3)[C:17]([C:22]([N:24]3[CH2:25][CH2:26][C:27]([F:30])([F:31])[CH2:28][CH2:29]3)=[O:23])=[CH:16]4)=[O:12])[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2773537(4-Methanesulfonamidophenyl)boronic acidHCID 68683577[5-(4-Cyclobutyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Product 1

HCID 68682762N-{4-[5-(4-Cyclobutyl-piperazine-1-carbonyl)-2-(4,4-difluoro-piperidine-1-carbonyl)-indol-1-yl]-phenyl}-methanesulfonamideYield 19%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized in analogy to example 66, from [5-(4-cyclobutyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 41), 4-(methanesulfonylamino)phenylboronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a colorless foam (19%).

Sources & evidence

ORD record
ord-f0af9f9556d7431d91b2f05b3731c37c
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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