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Water → HCID 86731235, Verbindung

HRID 2277179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2277179
Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)=[CH:13][CH:12]=3)[O:10][C:4]=2[CH:3]=1.[CH3:22][C@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]#[CH:25].C(N(CC)CC)C.O>CN(C=O)C.[Cu]I>[CH:19]1([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:9]3[O:10][C:4]4[CH:3]=[C:2]([C:25]#[C:24][C@@H:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:22])[N:7]=[CH:6][C:5]=4[N:8]=3)=[CH:12][CH:13]=2)[CH2:21][CH2:20]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 10986677tert-Butyl (2S)-but-3-yn-2-ylcarbamateHCID 86731236HCID 86731236, Verbindung

Produkt 1

HCID 86731235HCID 86731235, VerbindungAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 6-chloro-2-(4-(cyclopropylmethoxy)phenyl) [1,3]oxazolo[4,5-c]pyridine (700 mg), tert-butyl (2S)-but-3-yn-2-ylcarbamate (1.13 g) and triethylamine (0.649 g) in DMF (10 mL) were added bistriphenylphosphinedichloropalladium(II) (163 mg) and copper(I) iodide (88.7 mg), and the mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and subjected to silica gel column chromatography (NH, ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate to give the title compound (132 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained solid was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-beb092f8a1e8402e8755fb1ae1d3b1f2
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133129B2

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