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Sodium hydride → [1-Cyclobutylmethyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone

HRID 1820441
Notes
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Reaction equation

HRID 1820441 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:34][CH:35]1[CH2:38][CH2:37][CH2:36]1>CN(C)C=O>[CH:35]1([CH2:34][N:11]2[C:12]3[C:17](=[CH:16][C:15]([C:19]([N:21]4[CH2:22][CH2:23][N:24]([CH:27]([CH3:28])[CH3:29])[CH2:25][CH2:26]4)=[O:20])=[CH:14][CH:13]=3)[CH:18]=[C:10]2[C:8]([N:5]2[CH2:6][CH2:7][C:2]([F:1])([F:30])[CH2:3][CH2:4]2)=[O:9])[CH2:38][CH2:37][CH2:36]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734658(Bromomethyl)cyclobutaneHCID 68680853(4,4-Difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

Product 1

HCID 68682497[1-Cyclobutylmethyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneYield 69%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

The title compound was synthesized in analogy to example 51, from (4,4-difluoro-piperidin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 32), sodium hydride and (bromomethyl)cyclobutane in N,N-dimethylformamide, to give the desired product as a colorless foam (69%).

Sources & evidence

ORD record
ord-ab2023138d5248ccad23485e05bfd9c9
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07601711B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes