Potassium Phosphate, Tribasic → 5-Cyclopropylnicotinonitrile

HRID 931137Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931137
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1>[CH:10]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:7]=2)[C:8]#[N:9])[CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 7367935-BromonicotinonitrileHCID 2760897Cyclopropylboronic acid

Produkt 1

HCID 574196235-CyclopropylnicotinonitrileAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-5-cyanopyridine (1 g, 5.3 mmol) in tetrahydrofuran was added cyclopropyl boronic acid (0.5 g, 5.6 mmol) and potassium phosphate (1.08 g, 15.9 mmol). The resulting solution was degassed with nitrogen for 10 minutes and then palladium (II) acetate and S-phos were added. The reaction mixture was refluxed for 16 h. The reaction mixture was diluted with water, extracted with ethyl acetate and concentrated under reduced pressure. The crude material was purified via column chromatography to afford 5-cyclopropylnicotinonitrile (0.45 g, 58%). MS (ES+) (M+H) 145.1774.

Aufarbeitung

  1. customThe resulting solution was degassed with nitrogen for 10 minutes
  2. additionpalladium (II) acetate and S-phos were added
  3. temperatureThe reaction mixture was refluxed for 16 h
  4. additionThe reaction mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fb23e4a5782d4d198fae2eb89dc570e7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

Notizen zur Reaktion

Wird geladen…