Toluene → HCID 67021739, Verbindung

HRID 536908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536908
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]3[CH2:14][O:15][CH2:16][CH:9]2[CH2:10][O:11][CH2:12]3)[N:5]=[C:4]([N:17]2[CH:22]3[CH2:23][O:24][CH2:25][CH:18]2[CH2:19][O:20][CH2:21]3)[N:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>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.CCO>[CH:22]12[N:17]([C:4]3[N:5]=[C:6]([N:8]4[CH:13]5[CH2:14][O:15][CH2:16][CH:9]4[CH2:10][O:11][CH2:12]5)[N:7]=[C:2]([C:30]4[CH:31]=[CH:32][C:27]([NH2:26])=[CH:28][CH:29]=4)[N:3]=3)[CH:18]([CH2:25][O:24][CH2:23]1)[CH2:19][O:20][CH2:21]2

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 87239692HCID 87239692, Verbindung

Produkt 1

HCID 67021739HCID 67021739, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a 10 mL vial were added 9,9′-(6-chloro-1,3,5-triazine-2,4-diyl)bis(3,7-dioxa-9-azabicyclo[3.3.1]nonane) (150 mg, 0.406 mmol), 4-aminophenylboronic acid pinacol ester (133 mg, 0.61 mmol), Pd(PPh3)4 (10 mg), toluene (1 mL), EtOH (1 mL) and 2M Na2CO3 aqueous solution (0.305 mL). The resulting mixture was heated at 120° C. for 20 minutes in microwave oven. The reaction mixture was cooled to room temperature. The aqueous phase was extracted with EtOAc, and the combined organic phases were dried over (MgSO4). The solvent was removed under reduced pressure and the residue was subjected to HPLC separation to give 4-(4,6-di(3,7-dioxa-9-azabicyclo[3.3.1]nonan-9-yl)-1,3,5-triazin-2-yl)aniline as a white solid (120 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic phases were dried over (MgSO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was subjected to HPLC separation

Quellen und Nachweise

ORD-Eintrag
ord-a8547dc52d40481297bdd0a3720fdda9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859542B2

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