Cesium carbonate → Ethyl 5-fluoro-4-oxo-1-[4-(4-vinyl-1H-pyrazol-1-yl)benzyl]-1,4-dihydroquinoline-3-carboxylate

HRID 1969441

Reaktionsgleichung

[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22](I)[CH:21]=[N:20]2)=[CH:15][CH:14]=1.[CH:31]([B-](F)(F)F)=[CH2:32].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:30])[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[C:22]([CH:31]=[CH2:32])[CH:21]=[N:20]2)=[CH:15][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of ethyl 5-fluoro-1-[4-(4-iodo-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.080 g, 0.15 mmol), potassium vinyltrifluoroborate (0.013 g, 0.19 mmol), and 1 N cesium carbonate (0.31 mL, 0.31 mmol) in 2 mL of acetonitrile under nitrogen was added bis(tri-tert-butylphosphoranyl)palladium (10 mol %). The reaction mixture was stirred at 100° C. for 14 hours, cooled to room temperature, and concentrated in vacuo to provide the title compound (crude) which gave a mass ion (ES+) of 417.9 for M+H+. This compound could be further hydrolyzed to the corresponding carboxylic acid, as described in Example 1.

Aufarbeitung

temperaturecooled to room temperature
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-c315ae412dc74745811454f878483126
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08426598B2

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