Trifluoroacetic acid → 1-Ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-5-methylindolin-2-one

HRID 1523053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523053
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5](=[O:13])[C:4]1=[O:14])[CH3:2].[CH3:15][O:16][C:17]1[C:18]([CH3:23])=[N:19][CH:20]=[CH:21][CH:22]=1.FC(F)(F)C(O)=O>O1CCOCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5]([OH:13])([CH2:23][C:18]2[C:17]([O:16][CH3:15])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4]1=[O:14])[CH3:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 24713051-ethyl-5-methyl-2,3-dihydro-1H-indole-2,3-dioneHCID 30152703-Methoxy-2-methylpyridine

Produkt 1

HCID 863003991-Ethyl-3-hydroxy-3-((3-methoxypyridin-2-yl)methyl)-5-methylindolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a flame dried sealed tube cooled under argon was added the 1-ethyl-5-methylindoline-2,3-dione (0.03 grams, 0.15 mmol) and 3-methoxy-2-methyl-pyridine (0.072 grams, 0.59 mmol, purchased from Fisher Scientific) and 0.5 mL of 1,4 dioxane. After the addition of trifluoro acetic acid (2 μL) the vessel was sealed and heated to 110° C. for 48 hours. The reaction was then concentrated. 1H-NMR δ 8.21 (s, 1H), 7.35 (bs, OH), 7.26 (m, 1H), 7.20 (d, 1H), 7.09 (d, 1H), 6.90 (s, 1H), 6.75 (d, 1H), 3.78 (s, 3H), 3.77 (m, 2H), 3.34 (d, 1H), 3.18 (d, 1H), 2.27 (s, 3H), 1.28 (t, 3H). Calculated mass for C18H20N2O3, 312.15. Observed 313.1 (M+1).

Aufarbeitung

  1. customTo a flame dried
  2. customsealed tube
  3. temperaturecooled under argon
  4. customwas sealed
  5. concentrationThe reaction was then concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be035068f5c04a0195ae069178012af1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079853B2

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