Cesium carbonate → HCID 57831043, Verbindung

HRID 600394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600394
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[C:25](=[NH:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25](=[N:38][C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1)([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 578292211-(2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-yl)-2,2-dimethylpropane-1-one

Produkt 1

HCID 57831043HCID 57831043, VerbindungAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.576 g, 1.40 mmol), benzophenone imine (0.26 mL, 1.54 mmol), cesium carbonate (0.912 g, 2.80 mmol), palladium acetate (0.031 g, 0.14 mmol) and BINAP (0.087 g, 0.14 mmol) in 14 mL of tetrahydrofuran was stirred at 90° C. in a sealed tube for 64 h then concentrated. The resulting residue was taken up in 30 mL of ethyl acetate and sequentially washed with 30 mL of water and 30 mL of a sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated to a residue. Column chromatography (10→25% EtOAc/hexanes) afforded 0.670 g (93%) of 1-[2-(benzhydrylidene-amino)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil.

Aufarbeitung

  1. concentrationthen concentrated
  2. washsequentially washed with 30 mL of water and 30 mL of a sat. aq. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

Quellen und Nachweise

ORD-Eintrag
ord-2f4f7688aacc424994bf6c96cc3b9cf4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902197B2

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