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Ethanol → HCID 21947806, Verbindung

HRID 2215150
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2215150
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:24]1(B(O)O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+]>[C:32]1([C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[CH2:14][N:13]4[CH:21]=[CH:22][CH:23]=[C:12]4[CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[C:33]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Produkt 1

HCID 21947806HCID 21947806, VerbindungAusbeute 22,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178476740
HCID 178476740, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of (6-chloro-pyridin-3-yl)-[10,11-dihydro-5H-pyrrolo{2,1-c][1,4]benzodiazepin-10-yl]methanone of Step A (0.645 g, 1.9 mmol) and naphthalene boronic acid (0.372 g, 2.1 mmol) in a mixture of toluene (1.2 mL), ethanol (2 mL) and 1M aqueous sodium carbonate (0.4 mL) was sparged with nitrogen for 10 minutes. To this was added palladium(I) acetate (0.026 g, 0.1 mmol). The mixture was heated at reflux under a static pressure of nitrogen for 48 hrs. The reaction was diluted with ethyl acetate and water. The organic layer was washed with saturated aqueous sodium bicarbonate then water. The sample was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a brown oil. Flash chromatography of the residue on silica gel eluting with 20–50% ethyl acetate in hexane, yielded 0.180 g of a solid which was recrystallized from chloroform to provide the title compound as off white crystals, m.p. 155–158° C.

Aufarbeitung

  1. customwas sparged with nitrogen for 10 minutes
  2. temperatureThe mixture was heated
  3. temperatureat reflux under a static pressure of nitrogen for 48 hrs
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialThe sample was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-be7cb4cc0866419bb469cd2650b2eed2
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109193B2

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