Pyridine → [5-([1,4]Bipiperidinyl-1'-carbonyl)-1-(6-chloro-pyridin-3-yl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 1820497Notes

Reaction equation

HRID 1820497 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][C:19]([C:24]([N:26]3[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28][CH2:27]3)=[O:25])=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][N:36]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:38]3[CH:37]=[N:36][C:35]([Cl:34])=[CH:40][CH:39]=3)[C:19]([C:24]([N:26]3[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28][CH2:27]3)=[O:25])=[CH:18]4)=[O:14])[CH2:9][CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 38450342-Chloropyridine-5-boronic acidHCID 68681611[5-([1,4']bipiperidinyl-1'-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Product 1

HCID 86615811[5-([1,4]Bipiperidinyl-1'-carbonyl)-1-(6-chloro-pyridin-3-yl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneYield 57%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was synthesized in analogy to example 66, from [5-([1,4′]bipiperidinyl-1′-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 168), 2-chloropyridine-5-boronic acid, copper(II) acetate and pyridine in dichloromethane, to give the desired product as a brown oil (57%).

Sources & evidence

ORD record
ord-2d8ca5300cd3499189de031d8a61d339
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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