Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate → Methyl 2-[6-(aminomethyl)-5-fluoropyridin-3-yl]-6-fluorobenzoate

HRID 1711485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711485
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[F:20])#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[F:20]

Komponenten

4

Edukt 1

HCID 21075884Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate

Produkt 1

HCID 21075883Methyl 2-[6-(aminomethyl)-5-fluoropyridin-3-yl]-6-fluorobenzoateAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 21705897Ammonia methanolLösungsmittel

Versuchsvorschrift

To a stirred solution of the above ester (0.75 g, 2.7 mmol) in NH3/MeOH (5 mL, 2.0 M) was added Raney 2800 nickel (slurry in water). The mixture was stirred under a H2 atmosphere (balloon) at room temperature for 6 hours. The mixture was then filtered through glass filter paper, washing with additional MeOH. The resultant solution was concentrated under vacuum and azeotroped three times with toluene to provide crude title compound (0.65 g, 2.34 mmol).

Aufarbeitung

  1. filtrationThe mixture was then filtered through glass
  2. filtrationfilter paper
  3. washwashing with additional MeOH
  4. concentrationThe resultant solution was concentrated under vacuum
  5. customazeotroped three times with toluene

Quellen und Nachweise

ORD-Eintrag
ord-b67283e28ac84eacb795c4b32cc94867
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790754B2

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