Dimethylformamide → HCID 68701183, Verbindung

HRID 14504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14504
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21](=[O:22])[C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH2:15][CH2:14][O:13]4)[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.[CH3:26][N:27](C)C=O>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].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N>[CH:23]([C:9]1[O:10][C:11]2[C:20]([C:21](=[O:22])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([C:26]#[N:27])=[CH:3][CH:4]=1)=[CH:19][CH:18]=[C:17]1[C:12]=2[O:13][CH2:14][CH2:15][NH:16]1)([CH3:25])[CH3:24]

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 167498117-(4-Chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one

Produkt 1

HCID 68701183HCID 68701183, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 7-(4-chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one (71.7 mg, 0.202 mmol), tris(dibenzylideneacetone)dipalladium (0) (92.2 mg, 0.101 mmol), 1,1′-bis(diphenylphosphino)ferrocene (112 mg, 0.202 mmol) and zinc cyanide (24 mg, 0.204 mmol) in N,N-dimethylformamide (2.5 ml) is heated at 180° C. for 40 min under microwave irradiation in an Emrys Optimizer instrument (Biotage AB, Uppsala, Sweden). The mixture is filtered through a short pad of Celite, which is then thoroughly washed through with ethyl acetate. The filtrate is washed successively with water and brine. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient) to afford the title compound.

Aufarbeitung

  1. filtrationThe mixture is filtered through a short pad of Celite, which
  2. washis then thoroughly washed through with ethyl acetate
  3. washThe filtrate is washed successively with water and brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3ba665b8e1054935a1a2c1ba98a264df
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732435B2

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