Sodium hydride → HCID 68683299, compound

HRID 1820485Notes

Reaction equation

HRID 1820485 reaction equation
[F:1][C:2]1([F:32])[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[CH2:25][CH2:24][CH2:23][C@H:22]2[CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:20])=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:36][CH:37]1[CH2:40][CH2:39][CH2:38]1>CN(C)C=O>[CH:37]1([CH2:36][N:11]2[C:12]3[C:17](=[CH:16][C:15]([C:19]([N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]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:32])[CH2:3][CH2:4]2)=[O:9])[CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734658(Bromomethyl)cyclobutaneHCID 68680741HCID 68680741, compound

Product 1

HCID 68683299HCID 68683299, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 51, from [2-(4,4-difluoro-piperidine-1-carbonyl)-1H-indol-5-yl]-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (example 44), sodium hydride and (bromomethyl)cyclobutan in N,N-dimethylformamide, to give the desired product as a white foam (73%).

Sources & evidence

ORD record
ord-3653eeb44f574f1888b544102042e1c0
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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