1-Bromo-2,3-dichlorobenzene → 1-(2,3-Dichlorophenyl)-[1,4]diazepine

HRID 16119

Reaktionsgleichung

Reaktionsgleichung von HRID 16119
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[Cl:9].C(OC([N:17]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=[CH:18]1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1>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]>[Cl:9][C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[N:20]1[CH:21]=[CH:22][CH:23]=[N:17][CH:18]=[CH:19]1

Komponenten

6

Edukt 3

HCID 420661-Bromo-2,3-dichlorobenzeneHCID 57499755[1,4]Diazepine-1-carboxylic acid tert-butylesterHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl

Produkt 1

HCID 686314891-(2,3-Dichlorophenyl)-[1,4]diazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.25 g (10 mmol) 1-bromo-2,3-dichloro-benzene was dissolved in dry toluene (50 ml), 2.3 (11 mmol) of [1,4]diazepine-1-carboxylic acid tert-butylester was added followed by 0.2 g BINAP (2,2-bis(diphenylphosphino)-1,1′-binaphtyl), 85 mg tris(dibenzylideneacetone)dipalladium(0) and 1.2 g (12 mmol) sodium-tert-butoxyde. The reaction mixture was refluxed for eight hours and filtered. The organic layer was washed with water, dried and evaporated in vacuo. The residue was purified by chromatography and deprotected at 10° C. using 20 ml ethylacetate saturated with gaseous hydrochloric acid, the precipitate was filtered giving 2.1 g (yield: 75%) hydrochloride salt of the title compound, melting at 182-3° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for eight hours
  2. filtrationfiltered
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography
  7. customdeprotected at 10° C.
  8. filtrationthe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-7a73e7e5afb045feb1e989fcb8ce389d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737142B2

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