5-Bromopyridine-2-carboxamide → HCID 58149557, Verbindung

HRID 1920082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920082
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[OH:11][CH:12](O)[C:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=[O:14]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:12]([OH:11])[C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[O:14])=[O:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 7351515-Bromopyridine-2-carboxamideHCID 5684550216208-20-1

Produkt 1

HCID 58149557HCID 58149557, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-bromopicolinamide 111 (0.588 g, 2.92 mmol) and 2,2-dihydroxy-1-(naphthalen-1-yl)ethanone 112 (1.20 g, 5.67 mmol) in dioxane (20 mL) were heated at 100° C. for 18 hours. The dioxane was removed under vacuum and the residue was dissolved in chloroform and methanol and concentrated onto silica gel. The material was purified by auto flash system (CH2Cl2 to 1% MeOH: CH2Cl2) to give 5-bromo-N-(1-hydroxy-2-(naphthalen-1-yl)-2-oxoethyl)picolinamide 113 as a tan solid (0.74 g, 66%).

Aufarbeitung

  1. customThe dioxane was removed under vacuum
  2. dissolutionthe residue was dissolved in chloroform
  3. concentrationmethanol and concentrated onto silica gel
  4. customThe material was purified by auto flash system (CH2Cl2 to 1% MeOH: CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-1eeb2caaeeac4f419dd0e77c598cef4c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168795B2

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