Ethyl Acetate → 6-((6-Vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 456139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456139
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[NH4+].[Cl-].CCOC(C)=O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]([C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1)=[CH2:23]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 81998TributylvinyltinHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Produkt 1

HCID 593418146-((6-Vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineAusbeute 20,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a degassed solution 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (1200 mg, 3.52 mmol) in DMF (10 mL), was added Pd(PPh3)4 (610 mg, 0.528 mmol). The solution was stirred for 20 min, then tributyl(vinyl)stannane (1227 mg, 3.87 mmol) was added. The reaction mixture was heated to 120° C. for 5 h. NH4Cl(aq) was added to quench the reaction, followed by EtOAc. The reaction mixture was filtered through celite and the filtrate was washed with sat NaHCO3, sat NH4Cl. The organic layer was separated, dried over Na2SO4 and concentrated to give the crude product, which was purified with Analogix gel silica (Hexanes:EA) to afford 210 mg of title compound in 20% yield. LCMS (method B): [MH]+=288, tR=2.05 min.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe filtrate was washed with sat NaHCO3
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified with Analogix gel silica (Hexanes:EA)

Quellen und Nachweise

ORD-Eintrag
ord-1d49f23d7a1d42b693e5f6823b56b88c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497368B2

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