Reaktion #172017

ord-ab4b22353a46403f843250f7d345a5e4

Reaktionsgleichung

O
Water
N#Cc1cc(F)c(F)cc1Br
2-bromo-4,5-difluorobenzonitrile
CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1N
tert-butyl (1S,2R)-2-aminocyclohexylcarbamate
CCN(C(C)C)C(C)C
DIEA
→
CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1Nc1cc(Br)c(C#N)cc1F
tert-butyl (1S,2R)-2-(5-bromo-4-cyano-2-fluorophenylamino)cyclohexylcarbamate
Ausbeute 93.4%

Edukte

O
Water
N#Cc1cc(F)c(F)cc1Br
2-bromo-4,5-difluorobenzonitrile
CC(C)(C)OC(=O)N[C@H]1CCCC[C@H]1N
tert-butyl (1S,2R)-2-aminocyclohexylcarbamate
CCN(C(C)C)C(C)C
DIEA

Reagenzien

Keine

Lösungsmittel

CS(C)=O
DMSO

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprecipitation
  2. 2
    SonstigeThe precipitate was collected
  3. 3
    Sonstigedried on vacuum

Vorschrift

A solution of 2-bromo-4,5-difluorobenzonitrile (218 mg, 1.00 mmol), tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (214 mg, 1.00 mmol) and DIEA (0.300 mL, 1.72 mmol) in DMSO (2 mL) was stirred at 100 C for 18 h. Water was added to induce precipitation. The precipitate was collected and dried on vacuum to give tert-butyl (1S,2R)-2-(5-bromo-4-cyano-2-fluorophenylamino)cyclohexylcarbamate as a solid (385 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846928B2uspto-grants-2014_09