Trimethylsilylacetylene → 4-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

HRID 1513649

Reaktionsgleichung

Reaktionsgleichung von HRID 1513649
F[B-](F)(F)F.[C:6]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)[CH3:7].C[Si](C#C)(C)C.Br[C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH2:35][O:36][C:37]3[C:46]4[C:41](=[CH:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)=[N:33][N:34]=2)[CH:31]=1>O1CCOCC1.C(N(CC)CC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Cu]I>[C:6]([C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH2:35][O:36][C:37]3[C:46]4[C:41](=[CH:42][C:43]([O:47][CH3:48])=[CH:44][CH:45]=4)[N:40]=[CH:39][CH:38]=3)=[N:33][N:34]=2)[CH:31]=1)#[CH:7]

Komponenten

8

Edukt 3

HCID 66111TrimethylsilylacetyleneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 576910274-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

Produkt 1

HCID 866302634-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8471TriethylamineLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Step 1. Tri-t-butylphosphonium tetrafluoroborate (0.0377 g, 0.130 mmol), tris(dibenzylideneacetone)dipalladium (0.0594 g, 0.0649 mmol), trimethylsilyl acetylene (1.82 ml, 13.0 mmol), 4-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.500 g, 1.30 mmol) were taken up in dioxane (10 mL) and triethylamine (3 mL). Added CuI. Sealed in a tube and heated at 80° C. for 3 h. Concentrated. Took up in MeOH and added solid potassium carbonate (large excess). Allowed to stir for 30 min. Filtered through a plug of Celite and concentrated. Took up in 10% MeOH in DCM and filtered through a plug of silica gel to afford 4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline. MS m/z=331.0[M+1]+. Calc'd for C19H14N4O2: 330.3.

Aufarbeitung

  1. customSealed in a tube
  2. concentrationConcentrated
  3. additionadded solid potassium carbonate (large excess)
  4. filtrationFiltered through a plug of Celite
  5. concentrationconcentrated
  6. filtrationfiltered through a plug of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b6377f1829c543d68201cebab4002d00
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217177B2

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