Sodium hydride → [5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-cyclopropylmethyl-1H-indol-2-yl]-morpholin-4-yl-methanone

HRID 1820382Notes

Reaction equation

HRID 1820382 reaction equation
[CH:1]1([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][C:18]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[CH:17]4)=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH:33]1([CH2:36]Br)[CH2:35][CH2:34]1>CN(C)C=O>[CH:1]1([N:6]2[CH2:7][CH2:8][N:9]([C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:36][CH:33]3[CH2:35][CH2:34]3)[C:18]([C:23]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[O:24])=[CH:17]4)=[O:13])[CH2:10][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 24756895HCID 24756895, compound

Product 1

HCID 68682719[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1-cyclopropylmethyl-1H-indol-2-yl]-morpholin-4-yl-methanoneYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 51, from (4-cyclopentyl-piperazin-1-yl)-[2-(morpholine-4-carbonyl)-1H-indol-5-yl]-methanone (example 10), sodium hydride and cyclopropylmethyl bromide in N,N-dimethylformamide, to give the desired product as a colorless foam (38%).

Sources & evidence

ORD record
ord-ce7227f8f76849c4a7767ae0ad69df8c
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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