Cesium carbonate → HCID 68459554, Verbindung

HRID 501654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501654
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@H:9]1[C@H:21]([NH2:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[C:32]([CH3:33])=[C:31](I)[CH:30]=[CH:29][C:26]=1[C:27]#[N:28].C([O-])([O-])=O.[Cs+].[Cs+]>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[C@H](N(C)C)C1[CH-]C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@H:9]1[C@H:21]([NH:23][C:31]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:24])[C:32]=1[CH3:33])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 167319952-Chloro-4-iodo-3-methylbenzonitrileHCID 68457944HCID 68457944, Verbindung

Produkt 1

HCID 68459554HCID 68459554, VerbindungAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 44630263(S)-(R)-PpfaKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 80D (137 mg, 0.40 mmol) in nitrogen degassed toluene (3 mL) at rt was added 2-chloro-4-iodo-3-methyl-benzonitrile (122 mg, 0.44 mmol), Cs2CO3 (260 mg, 0.80 mmol) and Pd2(dba)3 (7.3 mg, 0.008 mmol) and (S)—N,N-dimethyl-1-[(R)-2-(diphenyphosphino)ferrocenyl]ethylamine (11 mg, 0.024 mmol). The reaction was degassed with nitrogen for 30 min, sealed and heated at 140° C. for 2 h under microwave conditions. The mixture was cool to rt, diluted with hexane and filtered through a layer of celite. The filtrate was evaporated to give the crude product. Purification by flash chromatography (10 g ISCO silica gel cartridge, 0-20% EtOAc in hexane gradient) gave the title compound 80E (36 mg): MS (ES) m/z 345 [M+H]+; HRMS calcd for C25H41N3O3ClSi 494.2606, found 494.2606.

Aufarbeitung

  1. customThe reaction was degassed with nitrogen for 30 min
  2. customsealed
  3. temperatureThe mixture was cool to rt
  4. additiondiluted with hexane
  5. filtrationfiltered through a layer of celite
  6. customThe filtrate was evaporated
  7. customto give the crude product
  8. customPurification by flash chromatography (10 g ISCO silica gel cartridge, 0-20% EtOAc in hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0e5e3028c98840dfb75095a0cd5c3dbc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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