Sodium bis(trimethylsilyl)amide → HCID 68748860, compound

HRID 624225

Reaction equation

HRID 624225 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:23]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34]Br)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:23](=[O:24])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:7](=[O:12])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 123789436-Bromoquinolin-2(1H)-one

Product 1

HCID 68748860HCID 68748860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromoquinolin-2(1H)-one (430 mg, 1.91 mmol) in tetrahydrofuran (8 ml) was added sodium bis(trimethylsilyl)amide (2.1 ml, 2.08 mmol). After 15 minutes, 4-(boc-amino)butyl bromide (403 mg, 1.6 mmol) was added. The solution was stirred for 15 hours, concentrated and purified by flash chromatography to provide the title compound.

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e9c68693dd3244a891f81831e016611e
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Linked notes

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