Tetrahydrofuran → 7-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

HRID 2176495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176495
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[N:14][C:15]([CH2:16][OH:17])=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[AlH4-].[Li+].C1([C:26]2[CH:31]=[CH:30][N:29]3N=N[C:34]([C:35]([O:37][CH3:38])=O)=[C:28]3[CH:27]=2)C=CC=CC=1.[CH2:39]1COC[CH2:40]1>CCOC(C)=O>[CH3:38][O:37][C:35]1[CH:34]=[C:28]2[C:27]([C:26]([O:17][CH2:16][C:15]3[N:14]=[N:13][N:10]4[CH:11]=[CH:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=34)=[CH:31][CH:30]=[N:29]2)=[CH:40][CH:39]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 28112Lithium aluminum hydrideHCID 67502437Methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylateHCID 67502444(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol

Produkt 1

HCID 576913407-Methoxy-4-((5-phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol. To a cooled (ice bath) suspension of lithium tetrahydroaluminate (0.0929 g, 2.45 mmol) in 2 mL THF (anhy) was added slowly a solution of methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate (0.310 g, 1.22 mmol) in 20 mL THF (internal temp remained <20 C). The mixture was allowed to stir in the ice bath 10 minutes. The mixture was diluted with EtOAc, washed with water, sat. NaHCO3, the organic layer dried over Na2SO4, and filtered. The aqueous layer still had uv activity so a solution of Rochelle's salt and EA were added and the mixture stirred 30 min. The organic layer was washed with sat NaHCO3, dried over Na2SO4, filtered, combined with main portion and evaporated. The title compound was isolated as a yellow solid.

Aufarbeitung

  1. temperatureTo a cooled
  2. washwashed with water, sat. NaHCO3
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. additionwere added
  6. washThe organic layer was washed with sat NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1f22ebaa08ce4fd79c87480eb2f516b8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09066954B2

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