3-Hydroxypyridine → HCID 69848762, compound

HRID 352227Notes

Reaction equation

HRID 352227 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:9]([O:11][C:12](=[O:21])[CH:13](Br)[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH3:10]>CN(C)C=O>[CH2:9]([O:11][C:12](=[O:21])[CH:13]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:10]

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 5360545SodiumHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Product 1

HCID 69848762HCID 69848762, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product was prepared in a manner similar to preparation 396 using the pre-formed sodium salt of the 3-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 dimethylformamide (20 mL). Column purification over SiO2 (0.5% then 1.5% methanol/chloroform) produced a yellow/orange oil (2.02; approx. 50% yield). MS(ES) calc'd: [M+H]+=259.2 m/z; [M−H]−=257.2 m/z. Found: 259.1 m/z; 257.1 m/z.

Workup

  1. customColumn purification over SiO2 (0.5%
  2. custom1.5% methanol/chloroform) produced a yellow/orange oil (2.02; approx. 50% yield)

Sources & evidence

ORD record
ord-9167976edf5044a48753a0e7255f6de0
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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