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Tetrahydrofuran → HCID 178421673, Verbindung

HRID 2112525
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2112525
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:20])[C:17]([CH3:19])=[CH:18][C:13]=2[N:12]=[C:11]2[N:21](CC=C)[NH:22][C:23]([CH3:24])=[C:10]2[N:9]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:20])[C:17]([CH3:19])=[CH:18][C:13]=2[N:12]=[C:11]2[NH:21][NH:22][C:23]([CH3:24])=[C:10]2[N:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 178456639HCID 178456639, Verbindung

Produkt 1

HCID 178421673HCID 178421673, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2.7 g (0.00716 mole) of 5-(2-chlorophenyl)-1,2-dihydro-3,7,8-trimethyl-1-(2-propenyl)-pyrazolo[3,4-b][1,4]benzodiazepine (XIVw), 0.155 g (0.00029 mole) of 1,3-bis(diphenylphosphino)propane nickel (II) chloride and 140 mL of anhydrous tetrahydrofuran at −40° C. was added 43 mL of 1M diisobutylaluminum hydride in toluene. The mixture was stirred at 0° C. for 6 hours and then quenched by the careful addition of ice water. The mixture was extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-dichloromethane (1:1) to give 1.5 g of 5-(2-chlorophenyl)-1,2-dihydro-3,7,8-trimethyl-pyrazolo[3,4-b][1,4]benzodiazepine (IVw) as an orange solid. MH+/Z=337.

Aufarbeitung

  1. customquenched by the careful addition of ice water
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate-dichloromethane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f9c8b93143ed4a3fb30525e2f2e8244b
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07524840B2

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