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Water → HCID 70818582, Verbindung

HRID 591062
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 591062
C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1.[C:20]([O:24][CH:25]([C:31]1[C:35](B2OC(C)(C)C(C)(C)O2)=[C:34]([CH3:45])[S:33][C:32]=1[CH3:46])[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:20]([O:24][CH:25]([C:31]1[C:35]([C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)=[C:34]([CH3:45])[S:33][C:32]=1[CH3:46])[C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:23])([CH3:22])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-oneHCID 70818507HCID 70818507, Verbindung

Produkt 1

HCID 70818582HCID 70818582, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under argon atmosphere, sodium carbonate (11.2 mg, 0.11 mmol), water (0.7 mL), and 6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one (24.2 mg, 0.11 mmol) were added to a solution of ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (48 mg, 0.10 mmol) in N,N-dimethylformamide (2.1 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (23.4 mg, 0.02 mmol) was added. The mixture was heated at 100° C. for 15 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30) to afford the desired product (35a) (14 mg, 0.03 mmol, 33%).

Aufarbeitung

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30)

Quellen und Nachweise

ORD-Eintrag
ord-45fe52d8a88a4d7f82422429df92820b
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09238026B2

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