Di-tert-butyl azodicarboxylate → HCID 89611118, Verbindung

HRID 869064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869064
[Br:1][C:2]1[CH:7]=[C:6](B(O)O)[C:5]([O:11][CH3:12])=[CH:4][N:3]=1.[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:28][C:25]([O:24][C:22]([N:13]([C:6]1[C:5]([O:11][CH3:12])=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:23])([CH3:26])[CH3:27]

Komponenten

5

Edukt 2

HCID 97268Di-tert-butyl azodicarboxylateHCID 44119383(2-Bromo-5-methoxypyridin-4-yl)boronic acid

Produkt 1

HCID 89611118HCID 89611118, VerbindungAusbeute 11,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 2-bromo-5-methoxypyridine-4-boronic acid (10 g, 43.1 mmol), di-tert-butyl azodicarboxylate (9.93 g, 43.1 mmol), and copper(II) acetate (7.48 mg, 0.041 mmol) in MeOH (150 mL) was stirred 20 h at 50° C., filtered, concentrated, diluted with brine (100 mL), and extracted with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→3:1) to provide 2.13 g of the title compound. tR: 1.21 min (LC-MS 4); ESI-MS: 418.2 [M+H]+ (LC-MS 4); Rf=0.67 (hexane/EtOAc, 1:1).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additiondiluted with brine (100 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→3:1)

Quellen und Nachweise

ORD-Eintrag
ord-df590c170538427a9f77e7e09472edef
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969341B2

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