Sodium hydride → [5-([1,4']Bipiperidinyl-1'-carbonyl)-1-(2,2,2-trifluoro-ethyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 2241651Notes

Reaction equation

HRID 2241651 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.[H-].[Na+].CS(O[CH2:41][C:42]([F:45])([F:44])[F:43])(=O)=O>CN(C)C=O>[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]([CH2:41][C:42]([F:45])([F:44])[F:43])[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

5

Reactant 3

HCID 24758Sodium hydrideHCID 5565652,2,2-Trifluoroethyl MethanesulfonateHCID 68681611[5-([1,4']bipiperidinyl-1'-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Product 1

HCID 68681708[5-([1,4']Bipiperidinyl-1'-carbonyl)-1-(2,2,2-trifluoro-ethyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 51, from [5-([1,4′]bipiperidinyl-1′-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone (example 168), sodium hydride and 2,2,2-trifluoroethyl methanesulfonate in N,N-dimethylformamide to give the desired product as a colorless solid (89%).

Sources & evidence

ORD record
ord-3c7f93b1f595405dbf2ad0ffbb716a00
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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