Methyl propiolate → Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-5-carboxylate

HRID 386047

Reaktionsgleichung

Reaktionsgleichung von HRID 386047
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[N:6]=1)=[N+:2]=[N-:3].[C:12]([O:16][CH3:17])(=[O:15])[C:13]#[CH:14]>C1(C)C=CC=CC=1>[Br:11][C:7]1[N:6]=[C:5]([CH2:4][N:1]2[C:13]([C:12]([O:16][CH3:17])=[O:15])=[CH:14][N:3]=[N:2]2)[CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 13536Methyl propiolateHCID 453574032-(Azidomethyl)-6-bromopyridine

Produkt 1

HCID 59525904Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-(Azidomethyl)-6-bromopyridine (Example 470 Step 1) (600 mg, 2.82 mmol) and methyl propiolate (355 μL, 4.22 mmol) were combined in toluene (10 mL) and stirred at reflux overnight. The solvent was evaporated, and the residue was purified by flash chromatography (20-100% EtOAc/hexanes), whereby good separation of the two regioisomeric products was achieved. TLC, LC/MS, and 1H NMR analysis confirmed that the first spot (less polar, higher Rf) corresponded to the desired regioisomer. The title compound was isolated as a colorless oil.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (20-100% EtOAc/hexanes), whereby good separation of the two regioisomeric products

Quellen und Nachweise

ORD-Eintrag
ord-b1b63a839673446cbd034ed3685dcd55
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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