1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58115030, Verbindung

HRID 1808696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1808696
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.C(C1CCCCN1C)C#C.[CH2:29]1[CH2:39][CH2:38][N:37]2[C:32](=N[CH2:34][CH2:35][CH2:36]2)[CH2:31][CH2:30]1>CC(N(C)C)=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][CH:32]1[CH2:30][CH2:29][CH2:39][CH2:38][N:37]1[CH2:36][C:35]#[C:34][C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 575165972-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazineHCID 866501572228977-48-6

Produkt 1

HCID 58115030HCID 58115030, VerbindungAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (250 mg, 0.76 mmol), 2-propargyl-1-methyl-piperidine (105 mg, 0.76 mmol), copper iodide (15 mg, 0.076 mmol), dichlorobis-(triphenylphosphine)palladium (II) (11 mg, 0.02 mmol) and DBU (0.34 mL, 2.28 mmol) in dry dimethyl acetamide (3 mL). The mixture was vacuum degassed and heated to 120° C. and stirred for 10 hours. The mixture was cooled to ambient and quenched via the addition of water (45 ml) and ethyl acetate (45 ml). The material was shaken in a separatory funnel, and the ethyl acetate phase was collected. The aqueous phases were back extracted with ethyl acetate (2×40 ml), the organics combined, dried (MgSO4), filtered and stripped. The remainder was purified by preparative TLC using 15% ethyl acetate in hexanes as eluant. The plates were re-developed consecutively with 40% and then 60% ethyl acetate in hexanes. The product band was collected to provide 185 mg of (+/−)-2-[3-(2-methyl-piperidin-1-yl)-prop-1-ynyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a golden yellow oil. MS (M+H)+=385

Aufarbeitung

  1. customdegassed
  2. temperatureThe mixture was cooled to ambient and
  3. customquenched via the addition of water (45 ml) and ethyl acetate (45 ml)
  4. stirringThe material was shaken in a separatory funnel
  5. customthe ethyl acetate phase was collected
  6. extractionThe aqueous phases were back extracted with ethyl acetate (2×40 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe remainder was purified by preparative TLC
  10. customThe product band was collected

Quellen und Nachweise

ORD-Eintrag
ord-7e43a05ef139474a9bb1e82ed3a2df0e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361962B2

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