Sodium hydride → HCID 69848905, Verbindung

HRID 352226

Reaktionsgleichung

Reaktionsgleichung von HRID 352226
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH2:10]([O:12][C:13](=[O:22])[CH:14](Br)[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:11]>CN(C=O)C>[CH2:10]([O:12][C:13](=[O:22])[CH:14]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:11]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetateHCID 178516071HCID 178516071, Verbindung

Produkt 1

HCID 69848905HCID 69848905, VerbindungAusbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (520 mg; 21.8 mmol; 1.4 equiv) was stirred with 2-hydroxypyridine (1.73 g; 18.2 mmol; 1.2 equiv) in DMF (30 mL) for 15 min. This solution was added to an aliquot of bromo-pyridin-3-yl-acetic acid ethyl ester (approx. 3.6 g; 15 mmol) in DMF (20 mL). After stirring overnight, at rt., the resulting opaque black solution was concentrated in vacuo, dissolved in 20% isopropyl alcohol/chloroform, washed 5 times with saturated NaHCO3(aq), washed twice with saturated NaCl(aq), and dried over Na2SO4(s). After filtration, the solution was concentrated in vacuo and purified by SiO2 column chromatography on two consecutive columns with a 1% methanol/chloroform mobile phase and then an ethyl acetate/hexanes mobile phase (30%, 40%, 50% step gradient). A light yellow oil (134 mg; approx. 3% yield) was isolated. MS(ES) calc'd: [M+H]+=259.2 m/z. Found: 259.1 m/z.

Aufarbeitung

  1. concentration, the resulting opaque black solution was concentrated in vacuo
  2. dissolutiondissolved in 20% isopropyl alcohol/chloroform
  3. washwashed 5 times with saturated NaHCO3(aq)
  4. washwashed twice with saturated NaCl(aq)
  5. dry with materialdried over Na2SO4(s)
  6. filtrationAfter filtration
  7. concentrationthe solution was concentrated in vacuo
  8. custompurified by SiO2 column chromatography on two consecutive columns with a 1% methanol/chloroform mobile phase
  9. customA light yellow oil (134 mg; approx. 3% yield) was isolated

Quellen und Nachweise

ORD-Eintrag
ord-d94fa65d735a4eb0a54115991fc4408a
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

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