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

HRID 15987

Reaktionsgleichung

Reaktionsgleichung von HRID 15987
COCCOC.C([O-])([O-])=O.[Na+].[Na+].Br[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O>ClCCl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:14]1[N:19]=[C:18]2[N:20]([CH2:23][C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][CH:28]=[CH:27]4)[N:21]=[N:22][C:17]2=[N:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

Produkt 1

HCID 593418296-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of DME (3.0 mL) and 1 M aqueous Na2CO3 (0.88 mL) was degassed by bubbling in Argon for 10 minutes. The mixture was transferred via syringe to a vial containing 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.29 mmol), 2-fluorophenylboronic acid (45 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.2 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 3.5 hours. The crude reaction mixture was diluted with dichloromethane then washed with water. The dichloromethane was dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography using gradient elution with ethyl acetate and dichloromethane to afford 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (77 mg, 74%).

Aufarbeitung

  1. customwas degassed
  2. customby bubbling in Argon for 10 minutes
  3. customThe mixture was transferred via syringe
  4. customThe vial was capped
  5. customThe crude reaction mixture
  6. washthen washed with water
  7. dry with materialThe dichloromethane was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customThe residue was purified by column chromatography
  11. washelution with ethyl acetate and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-809f753e12c145829877418314079bb0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

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