Ethyl 2-bromo-2-(pyridin-3-yl)acetate → HCID 69848647, compound

HRID 352228Notes

Reaction equation

HRID 352228 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:20])[CH:12](Br)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:9]>[Na].CN(C=O)C>[CH2:8]([O:10][C:11](=[O:20])[CH:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH3:9]

Participants

5

Reactant 2

HCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetateHCID 178418642HCID 178418642, compound

Product 1

HCID 69848647HCID 69848647, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 5360545SodiumSolvent

Procedure

The product was formed in a manner similar to preparation 396 using the in situ-generated sodium salt of the 4-hydroxypyridine (2.13 g; 18.2 mmol; 1.2 equiv) and an aliquot of bromo-pyridin-3-yl-acetic acid ethyl ester (approx. 3.6 g; 15 mmol) in DMF (20 mL). Column chromatographic purification over SiO2 (1% methanol/chloroform) produced a yellow/orange oil (320 mg; approx. 8% yield). MS(ES) calc'd: [M+H]+=259.2 m/z. Pound: 259.1 m/z.

Workup

  1. customColumn chromatographic purification over SiO2 (1% methanol/chloroform)
  2. customproduced a yellow/orange oil (320 mg; approx. 8% yield)

Sources & evidence

ORD record
ord-f7f179a6ef874b2e980a7e2f78d4e6cf
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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