4-Bromo-3-fluorobenzotrifluoride → 4-(2-Fluoro-4-trifluoromethylphenyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 32654

Reaktionsgleichung

Reaktionsgleichung von HRID 32654
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[F:12].[CH3:13][C:14]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[C:14]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[F:12])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:13])[CH3:15]

Komponenten

6

Edukt 3

HCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342162-(Dicyclohexylphosphino)biphenyl

Produkt 1

HCID 534855174-(2-Fluoro-4-trifluoromethylphenyl)piperazine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5 g (20 mmol) 1-Bromo-2-fluoro-4-trifluoromethyl-benzene, 4.6 g (24.7 mmol) n-Boc-piperazine, 106 mg (0.1 mmol) Tris(dibenzylideneacetone)dipalladium chloroform complex 2.77 g (28.8 mmol) sodium-t-butoxide and 144 mg (0.4 mmol) 2-(Dicyclohexylphosphino)biphenyl in 50 ml toluene was heated for 16 h at 80° C. After cooling to room temperature the mixture was treated with 15 g Isolute HM-N and all volatiles were removed under vacuum. The residue was purified on silica eluting with a gradient of heptane/EtOAc to yield after evaporation 4.54 g (63%) of the title compound as white amorphous solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas treated with 15 g Isolute HM-N
  3. customall volatiles were removed under vacuum
  4. customThe residue was purified on silica eluting with a gradient of heptane/EtOAc
  5. customto yield
  6. customafter evaporation 4.54 g (63%) of the title compound as white amorphous solid

Quellen und Nachweise

ORD-Eintrag
ord-177df3555d644298b3f65361ea2c9a5f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427612B2

Verknüpfte Notizen

Wird geladen…