Sodium hydride → HCID 68681279, compound

HRID 2241646Notes

Reaction equation

HRID 2241646 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][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]>CN(C)C=O>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][CH2:37][CH2:36][N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:20])=[CH:14][CH:13]=2)[CH:18]=[C:10]1[C:8]([N:5]1[CH2:6][CH2:7][C:2]([F:1])([F:32])[CH2:3][CH2:4]1)=[O:9])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 68680741HCID 68680741, compound

Product 1

HCID 68681279HCID 68681279, compoundYield 44%

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 (2-bromoethoxy)-tert-butyldimethylsilane (commercially available) in N,N-dimethylformamide, to give the desired product as a colorless oil (44%).

Sources & evidence

ORD record
ord-a5cf56a8a6aa495bb8be06a75d869e16
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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