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

HRID 1820491Notes

Reaction equation

HRID 1820491 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+].[CH:36]1([CH2:39]Br)[CH2:38][CH2:37]1>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]([CH2:39][CH:36]3[CH2:38][CH2:37]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

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 68681611[5-([1,4']bipiperidinyl-1'-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

Product 1

HCID 68680919[5-([1,4']Bipiperidinyl-1'-carbonyl)-1-cyclopropylmethyl-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneYield 91%

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 cyclopropylmethyl bromide in N,N-dimethylformamide, to give the desired product as a colorless solid (91%).

Sources & evidence

ORD record
ord-a11fb60d419f462398859c36d1355355
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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