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Dimethyl Sulfoxide → Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

HRID 1481705
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1481705
N1C=CC=CC=1.CS(C)=O.[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH2:34][OH:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:11]([C:13]1[C:14]([C:25]2[CH:26]=[CH:27][C:28]3[N:29]([CH:31]=[C:32]([CH:34]=[O:35])[N:33]=3)[CH:30]=2)=[N:15][C:16]([O:23][CH3:24])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])[CH3:12]
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Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 71284396Methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

Produkt 1

HCID 89423055Methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To SO3-pyr complex (0.320 g, 2.01 mmol) was added pyridine (0.16 mL, 2.02 mmol) and DMSO (0.36 mL, 5.07 mmol). Slurry was stirred at room temperature 10 min before DCM (2.0 mL) was added and mixture was cooled to 0° C. Then solution of methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.346 g, 1.01 mmol), Hunig's base (0.60 mL, 3.44 mmol) and DMSO (0.36 mL, 5.07 mmol) in DCM (4.0 mL) was added dropwise. Reaction mixture was stirred at 0° C. 30 min and LC/MS showed complete consumption of starting material. DCM was removed under reduced pressure and residue was treated with H2O (10 mL). Solid which was formed was collected by filtration affording methyl 5-ethyl-6-(2-formylimidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.270 g) in 79% yield.

Aufarbeitung

  1. additionwas added
  2. customReaction mixture
  3. custom30 min and LC/MS
  4. customconsumption of starting material
  5. customDCM was removed under reduced pressure and residue
  6. additionwas treated with H2O (10 mL)
  7. customSolid which was formed
  8. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-02bf8e1feada4ce0a4c7224adea59084
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09409905B2

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