Cesium carbonate → (S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate

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Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[N:16]3[CH:17]=[CH:18][C:19]([O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:20][C:15]3=[N:14][CH:13]=1)[CH:8]=[CH:7]2.[NH2:26][C@@H:27]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28]1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].ClCCl>[CH3:25][O:24][CH2:23][CH2:22][O:21][C:19]1[CH:18]=[CH:17][N:16]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:2]([NH:26][C@H:27]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28]5)[CH:3]=[CH:4][CH:5]=4)[N:10]=3)=[CH:13][N:14]=[C:15]2[CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A stream of argon was passed through a mixture of 8-bromo-2-(7-(2-methoxyethoxy)-imidazo[1,2-a]pyridin-3-yl)quinoline (0.100 g, 0.2511 mmol), (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (0.05537 ml, 0.3264 mmol), Cs2CO3 (0.1145 g, 0.3515 mmol), Pd(OAc)2 (0.01127 g, 0.05022 mmol) and rac-BINAP (0.01564 g, 0.02511 mmol) in toluene (1 mL) for 15 minutes. The mixture was heated to 100° C. for 18 hours. The mixture was then allowed to cool to ambient temperature and dichloromethane was added. After stirring 30 minutes, the resulting mixture was filtered and the filtrate was concentrated to yield the title compound as an oil. MS APCI (+) m/z 504.1 (M+1) detected.

Aufarbeitung

temperatureto cool to ambient temperature
filtrationthe resulting mixture was filtered
concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-acfa1ff443ab40f290df50ff6e5d5270
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08138181B2

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