Potassium Acetate → 2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.Cl[C:31]1[N:36]=[C:35]([NH:37][CH2:38][C:39]2(O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[C:34]([F:46])=[CH:33][N:32]=1.CC([O-])=[O:49].[K+]>CC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:31]3[N:36]=[C:35]([NH:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]4[OH:49])[C:34]([F:46])=[CH:33][N:32]=3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[C:5]2=[N:6][CH:7]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
To a degassed solution of 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.15 g, 0.35 mmol), 1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol, 14a, (0.09 g, 0.35 mmol) and aqueous KOAc solution (1.04 mL of 1M solution, 1.04 mmol) in dimethylacetamide was added palladium triphenylphosphine (0.04 g, 0.03 mmol). The reaction mixture was heated at 140° C. in microwave for 15 min and then cooled to room temperature. The reaction mixture was filtered through celite, concentrated in vacuo, and the resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 14b:
Aufarbeitung
- temperaturecooled to room temperature
- filtrationThe reaction mixture was filtered through celite
- concentrationconcentrated in vacuo
- customthe resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile)
Quellen und Nachweise
- ORD-Eintrag
- ord-a2462e5501d647cd957faccd3bd9c721
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08829007B2
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