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Cesium carbonate → HCID 58386633, Verbindung

HRID 74678
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74678
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH3:47][O:48][C:49]1[CH:50]=[CH:51][C:52]2[NH:58][C:57](=[O:59])[N:56]([CH:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)[CH2:55][CH2:54][C:53]=2[CH:66]=1.Br[C:68]1[CH:69]=[N+:70]([O-:86])[CH:71]=[C:72]([C:74]([N:76]2[C:84]3[C:79](=[CH:80][C:81]([F:85])=[CH:82][CH:83]=3)[CH2:78][CH2:77]2)=[O:75])[CH:73]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:85][C:81]1[CH:80]=[C:79]2[C:84](=[CH:83][CH:82]=1)[N:76]([C:74]([C:72]1[CH:71]=[N+:70]([O-:86])[CH:69]=[C:68]([N:63]3[CH2:64][CH2:65][CH:60]([N:56]4[CH2:55][CH2:54][C:53]5[CH:66]=[C:49]([O:48][CH3:47])[CH:50]=[CH:51][C:52]=5[NH:58][C:57]4=[O:59])[CH2:61][CH2:62]3)[CH:73]=1)=[O:75])[CH2:77][CH2:78]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 673382653-Bromo-5-(5-fluoroindoline-1-carbonyl)-pyridine-1-oxide

Produkt 1

HCID 58386633HCID 58386633, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Under an argon atmosphere 5.0 mg (0.02 mmol) palladium(II)acetate and 14 mg (20 μmol) BINAP were added to 69 mg (0.25 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 84 mg (0.25 mmol) 3-bromo-5-(5-fluoroindoline-1-carbonyl)-pyridine-1-oxide and 0.12 g (0.38 mmol) caesium carbonate in 4.0 mL dioxane and the mixture was stirred overnight at 120° C. The reaction mixture was then evaporated down and the residue was dissolved in DMF/MeOH and purified by preparative HPLC-MS. The product-containing fractions were combined, the organic solvent was evaporated down and the residue was made alkaline with a 1N aqueous sodium hydroxide solution. The precipitate formed was suction filtered, washed with water and dried under HV.

Aufarbeitung

  1. customThe reaction mixture was then evaporated down
  2. dissolutionthe residue was dissolved in DMF/MeOH
  3. custompurified by preparative HPLC-MS
  4. customthe organic solvent was evaporated down
  5. customThe precipitate formed
  6. filtrationfiltered
  7. washwashed with water
  8. customdried under HV

Quellen und Nachweise

ORD-Eintrag
ord-1b72a5099787497b801e1bf8665068c0
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829006B2

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