Triethylamine → 5-(Benzyloxy)-3-bromopicolinonitrile

HRID 340222

Reaktionsgleichung

Reaktionsgleichung von HRID 340222
[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:21]#[N:22])(C)C.C(N(CC)CC)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]([C:21]#[N:22])=[N:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

Produkt 1

HCID 671177075-(Benzyloxy)-3-bromopicolinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 53-(benzyloxy)-5-bromopyridine 1-oxide (from step 2) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in hexane to give a mixture of two benzoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated en vacuo
  3. customthe residue was purified by a COMBIFLASH® system (ISCO)
  4. customto give
  5. additiona mixture of two benzoxy regioisomers, one of which

Quellen und Nachweise

ORD-Eintrag
ord-79c3e6c71bb74976b38875d78721c99b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895577B2

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