Sodium Carbonate → HCID 59603501, Verbindung

HRID 1692870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692870
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH2:15][CH2:14]3)[N:8]2[CH3:11])=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:3]=1.[C:31]1([S:37]([N:40]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42](B(O)O)=[CH:41]2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOC(C)=O.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>[CH3:11][N:8]1[C:7]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[CH2:15][CH2:14]2)=[N:6][C:5]2[C:9]1=[N:10][C:2]([C:42]1[C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:40]([S:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:39])=[O:38])[CH:41]=1)=[N:3][C:4]=2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 27762171-(phenylsulfonyl)-1H-indol-3-ylboronic acidHCID 596034954-(1-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

Produkt 1

HCID 59603501HCID 59603501, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a degassed suspension of 4-(1-((2-chloro-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine (249 mg, 0.571 mmol), 1-(phenylsulfonyl)-3-indoleboronic acid (189 mg, 0.628 mmol), 2M Na2CO3 aqueous solution (0.571 mL, 1.0 mmol) in toluene (5 mL) and ethanol (2 mL) was added Pd(PPh3)4 (33 mg, 0.029 mmol). The suspension was then stirred under nitrogen at 100° C. for 18 hours. The reaction mixture was then diluted with EtOAc and water. The layers were separated. The aqueous layer was extracted three times with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (25% MeOH in DCM) to give the title compound as a white solid (357 mg, 95.2%). LCMS: M+H+=657.2.

Aufarbeitung

  1. customThe layers were separated
  2. extractionThe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (25% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-522b9c2b6714482a80d4d8a9be9a5386
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158625B2

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