Tri-tert-butylphosphine tetrafluoroborate → isopropyl 4-{[6-(2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate
Reaktionsgleichung
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[NH:27]1[C:35]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1.O1CCOCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[C:18]([N:27]3[C:35]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28]3)[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A mixture of 2b (100 mg, 0.33 mmol), potassium tert-butoxide (0.1 g, 2.7 eq), 1-1 (0.35 mmol, 1.05 eq), tris(dibenzylideneacetone)dipalladium (32 mg, 0.1 eq), tri-t-butylphosphonium tetrafluoroborate (40 mg, 0.4 eq) and dioxane (1 mL) was heated at 80° C. for 18 h in a sealed vial. After allowing the reaction to cool down to room temperature, THF was added and the mixture was filtered. The filtrate was concentrated under a stream of nitrogen and the residue was taken up with 1 mL of THF and purified by preparative HPLC to afford 2-1.
Aufarbeitung
- customthe reaction
- temperatureto cool down to room temperature
- filtrationthe mixture was filtered
- concentrationThe filtrate was concentrated under a stream of nitrogen
- custompurified by preparative HPLC
- customto afford 2-1
Quellen und Nachweise
- ORD-Eintrag
- ord-f5e0ef3303a4442f8055515fed972946
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08481731B2
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