HCID 71007327, Verbindung → HCID 71007334, Verbindung

HRID 716188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716188
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH:7]=1>CCO.CCOC(C)=O.[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[C:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Komponenten

5

Edukt 1

HCID 71007327HCID 71007327, Verbindung

Produkt 1

HCID 71007334HCID 71007334, VerbindungAusbeute 111,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl) carbamate. A solution of tert-butyl (3-methyl-5-(3-nitropyridin-4-yl)phenyl)carbamate (198 mg, 0.60 mmol) in EtOH (5 mL) and EtOAc (5 mL) was degassed by bubbling N2 (g) through the solution for 10 min. Pd/C (10 wt %, 64 mg, 0.060 mmol) was added. A gas bag with a 3-way stopcock filled with H2 was attached to the flask. The flask was evacuated under vacuum and then back-filled with H2 (3×). The mixture was stiffed overnight at RT. The solution was degassed by bubbling N2 (g) through the solution for 10 min and was then filtered through celite. The solution was concentrated to afford tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl)carbamate (200 mg, 0.67 mmol, 111% yield) as an off-white foam. MS (ESI, pos. ion) m/z: 300.0 (M+1).

Aufarbeitung

  1. customby bubbling N2 (g) through the solution for 10 min
  2. additionA gas bag with a 3-way stopcock filled with H2
  3. customThe flask was evacuated under vacuum
  4. additionback-filled with H2 (3×)
  5. customThe solution was degassed
  6. customby bubbling N2 (g) through the solution for 10 min
  7. filtrationwas then filtered through celite
  8. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-886ab991c7fe4d059be079548838d921
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187486B2

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