1,4-Dioxane → HCID 178517858, Verbindung

HRID 1044388

Reaktionsgleichung

Reaktionsgleichung von HRID 1044388
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[Cl:12].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1.O1CCOCC1.C([Si](CC)(CC)[O:50][C@H:51]1[CH2:56][CH2:55][C@H:54]([N:57]2[CH2:61][CH2:60][C@:59]3([CH2:66][CH2:65][CH2:64][NH:63][CH2:62]3)[C:58]2=[O:67])[CH2:53][CH2:52]1)C.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=1[N:63]1[CH2:64][CH2:65][CH2:66][C@@:59]2([C:58](=[O:67])[N:57]([C@H:54]3[CH2:53][CH2:52][C@H:51]([OH:50])[CH2:56][CH2:55]3)[CH2:61][CH2:60]2)[CH2:62]1

Komponenten

7

Edukt 5

HCID 312751,4-DioxaneHCID 679882-Bromo-1-chloro-4-(trifluoromethyl)benzeneHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 178477595HCID 178477595, Verbindung

Produkt 1

HCID 178517858HCID 178517858, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

A mixture of 2-bromo-1-chloro-4-(trifluoromethyl)benzene (26 mg, 0.0001 mol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 0.000002 mol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (5 mg, 0.00001 mol) in 1,4-dioxane (0.5 mL, 0.006 mol) was stirred under N2 (g) for 20 min. To this mixture were added (5S)-2-{trans-4-[(triethylsilyl)oxy]cyclohexyl}-2,7-diazaspiro[4.5]decan-1-one (30 mg, 0.00008 mol) and sodium tert-butoxide (11.8 mg, 0.000123 mol), and the resulting mixture was degassed and stirred at 100° C. for 16 h. At this time 1M TBAF (tetra-n-butylammonium fluoride) in THF (0.3 mL) was added dropwise to the reaction mixture and the solution was stirred at rt for 1 h. The volatiles were removed in-vacuo and the residue was purified by prep-HPLC to afford the desired product. LC-MS: 431.1 (M+H)+.

Aufarbeitung

  1. customthe resulting mixture was degassed
  2. stirringstirred at 100° C. for 16 h
  3. additionAt this time 1M TBAF (tetra-n-butylammonium fluoride) in THF (0.3 mL) was added dropwise to the reaction mixture
  4. stirringthe solution was stirred at rt for 1 h
  5. customThe volatiles were removed in-vacuo
  6. customthe residue was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bdc603280d82498aabed7c836effbf81
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563570B2

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