Ethyl bromoacetate → HCID 22008786, compound

HRID 1602613Notes

Reaction equation

HRID 1602613 reaction equation
[O:1]=[C:2]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5][CH2:4][NH:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[O:1]=[C:2]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 220087643-[2-(1,8-Naphthyridin-2-yl)ethyl]piperidin-2-one

Product 1

HCID 22008786HCID 22008786, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-5 (0.28 g, 1.1 mmol) and DMF (10 mL) at -15° C. was treated with NaN(TMS)2 (1.2 mL, 1.2 mmol, 1M in hexanes) to give a red solution. After 30 min, the red solution was treated with ethyl bromoacetate (128 μL, 1.2 mmol), followed by continued stirring for 1 h. The reaction mixture was then quenched with sat. NH4Cl and then extracted with EtOAc (3×). The combined extracts were washed with brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% CH3OH/EtOAc) gave 1-6 as a yellow gum.

Workup

  1. customto give a red solution
  2. customThe reaction mixture was then quenched with sat. NH4Cl
  3. extractionextracted with EtOAc (3×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e9e0a44772e4bf8b0c677270d3086e6
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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