Potassium Carbonate → HCID 57386403, Verbindung

HRID 1771452

Reaktionsgleichung

Reaktionsgleichung von HRID 1771452
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[F:13][C:14]1[CH:19]=[C:18]([C:20]([O:22]C)=[O:21])[CH:17]=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[CH:19]=[C:18]([CH:17]=[CH:16][C:15]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[CH:3]=1)[C:20]([OH:22])=[O:21]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 248243452-Fluoro-4-(methoxycarbonyl)benzeneboronic acid

Produkt 1

HCID 57386403HCID 57386403, VerbindungAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Bromonaphthalen-2-ol (1 g, 4.48 mmol) was mixed with 880 mg of 2-fluoro-4-(methoxycarbonyl)phenylboronic acid (4.48 mmol), 1.2 g of K2CO3 (9.23 mmol), 120 mg of Pd(PPh3)4 (2.5 mol %), and then suspended in 17 mL of 1,4-Dioxane and 4 mL of H2O. The mixture was degassed 3× with argon and then heated to reflux while stirring for 1 hour. 4N NaOH (5 mL) was then added and stirred at room temperature for 2 hours, back extracted with EtOAc, and filtered through Celite. The basic aqueous solution was then acidified to pH=4.3 and the solids were filtered to give about 950 mg of off-white solid. This was triturated in 8 mL DCM and 2 mL EtOAc and filtered to yield about 830 mg of off-white Example 2 (65.8% overall yield). 1H-NMR (DMSO-d6 500 MHz): δ 13.31 (bs, 1H), 9.97 (bs, 1H), 8.05 (s, 1H), 7.90 (m, 2H), 7.80 (m, 3H), 7.64 (dt, 1H), 7.19 (m, 2H); MS (ESI): m/z 281.53 [MA]−.

Aufarbeitung

  1. customThe mixture was degassed 3× with argon
  2. temperatureheated
  3. temperatureto reflux
  4. addition4N NaOH (5 mL) was then added
  5. stirringstirred at room temperature for 2 hours
  6. extractionback extracted with EtOAc
  7. filtrationfiltered through Celite
  8. filtrationthe solids were filtered

Quellen und Nachweise

ORD-Eintrag
ord-8c738ed9021d4facad4e0820d977d500
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249132B2

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