Reaktion #10617

ord-c614d1288161409291394e06408d3032

Reaktionsgleichung

Brc1cccc2cnccc12
5-bromoisoquinoline
CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C
2-(di-tert-butylphosphino)biphenyl
CC(C)(C)OC(=O)N[C@H]1CC[C@H](N)CC1
Intermediate 40
CC(C)(C)OC(=O)N[C@H]1CC[C@H](N)CC1
trans-4-(N-tert-butoxycarbonylamino)cyclohexylamine
CC(C)(C)[O-].[Na+]
sodium tert-butoxide
→
CC(C)(C)OC(=O)N[C@H]1CC[C@H](Nc2cccc3cnccc23)CC1
title compound
Ausbeute 42.0%
CC(C)(C)OC(=O)N[C@H]1CC[C@H](Nc2cccc3cnccc23)CC1
trans-N-(tert-butoxycarbonyl)-N′-(5-isoquinolyl)-1,4-cyclohexanediamine
Ausbeute 42.0%

Edukte

—
tris(dibenzylideneacetone)palladium(0)
Brc1cccc2cnccc12
5-bromoisoquinoline
CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C
2-(di-tert-butylphosphino)biphenyl
CC(C)(C)OC(=O)N[C@H]1CC[C@H](N)CC1
Intermediate 40
CC(C)(C)OC(=O)N[C@H]1CC[C@H](N)CC1
trans-4-(N-tert-butoxycarbonylamino)cyclohexylamine
CC(C)(C)[O-].[Na+]
sodium tert-butoxide

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture was cooled to room temperature
  2. 2
    Sonstigepurified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Vorschrift

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (100 mg), tris(dibenzylideneacetone)palladium(0) (23 mg), 2-(di-tert-butylphosphino)biphenyl (29 mg), Intermediate 40 (122 mg) and sodium tert-butoxide (66 mg) in toluene was stirred with heating at 70° C. for 3.5 hours. The reaction mixture was cooled to room temperature and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (69 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094789B2uspto-grants-2006_08