Sodium Carbonate → HCID 67980883, Verbindung

HRID 2406232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2406232
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>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.O1CCOCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[CH2:10][N:11]2[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:25][CH:24]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 246945421-[(2-Bromophenyl)methyl]piperidin-4-one

Produkt 1

HCID 67980883HCID 67980883, VerbindungAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a 5 mL microwave vial equipped with a stir bar was added sodium carbonate (79 mg, 0.75 mmol). The vial was dried in an oven for 16 hours, then cooled to room temperature under nitrogen. 1-(2-Bromo-benzyl)-piperidin-4-one (100 mg, 0.37 mmol), 4-fluorophenyl boronic acid (52.2 mg, 0.37 mmol) and Pd(PPh3)4 (43 mg, 0.037 mmol) were added, followed by dioxane (5 mL) water (1 mL). The resulting mixture was degassed thoroughly with nitrogen and then heated in a microwave to 100° C. for 10 minutes. The reaction was filtered and the filtrate was concentrated. The crude residue was purified via flash chromatography (heptanes/EtOAc gradient) to afford the desired product as a yellow solid (58 mg, 40% yield). MS (ESI) ink (M+H+): 283.3.

Aufarbeitung

  1. customTo a 5 mL microwave vial equipped with a stir bar
  2. customThe vial was dried in an oven for 16 hours
  3. customThe resulting mixture was degassed thoroughly with nitrogen
  4. temperatureheated in a microwave to 100° C. for 10 minutes
  5. filtrationThe reaction was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe crude residue was purified via flash chromatography (heptanes/EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5ca16073ac8f44388a53db52f56b1ab9
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809352B2

Notizen zur Reaktion

Wird geladen…