Methyl iodide → HCID 11623273, Verbindung

HRID 1189098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189098
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]#[C:8][CH2:9][CH2:10][C:11]1[O:12][C:13]2[C:14](=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[N:15]=1.CI.[C:23]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH3:23][O:20][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][CH2:9][C:8]#[C:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[O:12][C:13]=2[CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11680534HCID 11680534, Verbindung

Produkt 1

HCID 11623273HCID 11623273, VerbindungAusbeute 47.368,398 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazol-4-ol (20 mg, 76 μmol, Example 70), methyl iodide (57 μL, 114 μmol) and K2CO3 (18 mg, 130 μmol) in DMF (2 mL) was stirred under reflux for 3 h. The reaction mixture was then allowed to cool to room temperature and was dissolved in DCM. The organic phase was washed with water, HCl 1N, saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 10 mg (36 mmol, 47%) of 4-methoxy-2-(4-(pyridin-2-yl)but-3-ynyl)benzo[d]oxazole as a brown solid.

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. washThe organic phase was washed with water, HCl 1N, saturated solution of NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Quellen und Nachweise

ORD-Eintrag
ord-f55bcfc91bce4ca88bf69462849673a8
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674106B2

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