Réaction #10665

ord-5bdc0731d83a4375b57f763a35e61dd4

Équation de réaction

CC(C)(C)OC(=O)N[C@H]1CC[C@H](Oc2cccc3cncc(Br)c23)CC1
Intermediate 121
CC(C)(C)OC(=O)N[C@H]1CC[C@H](Oc2cccc3cncc(Br)c23)CC1
trans-N-(tert-butoxycarbonyl)-4-[(4-bromo-5-isoquinolyl)oxy]cyclohexylamine
CCCC[C]([Sn])=C(CCCC)CCCC
tri(n-butyl)vinyltin
Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
2,6-di-tert-butyl-p-cresol
→
C=Cc1cncc2cccc(O[C@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12
title compound
C=Cc1cncc2cccc(O[C@H]3CC[C@H](NC(=O)OC(C)(C)C)CC3)c12
trans-N-(tert-butoxycarbonyl)-4-[(4-vinyl-5-isoquinolyl)oxy]cyclohexylamine

Réactifs

CC(C)(C)OC(=O)N[C@H]1CC[C@H](Oc2cccc3cncc(Br)c23)CC1
Intermediate 121
CC(C)(C)OC(=O)N[C@H]1CC[C@H](Oc2cccc3cncc(Br)c23)CC1
trans-N-(tert-butoxycarbonyl)-4-[(4-bromo-5-isoquinolyl)oxy]cyclohexylamine
CCCC[C]([Sn])=C(CCCC)CCCC
tri(n-butyl)vinyltin
Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
2,6-di-tert-butyl-p-cresol

Réactifs

c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
tetrakis(triphenylphosphine)palladium(0)

Solvants

Cc1ccccc1
toluene

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe solvent was evaporated under reduced pressure
  2. 2
    Autrethe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Mode opératoire

A solution of Intermediate 121 (500 mg), tri(n-butyl)vinyltin (518 μl, Tokyo Kasei Kogyo), tetrakis(triphenylphosphine)palladium(0) (28.1 mg) and 2,6-di-tert-butyl-p-cresol (3.2 mg, Tokyo Kasei Kogyo) in toluene (10 ml) was stirred at 110° C. for 3 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (409.5 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07094789B2uspto-grants-2006_08