Cesium carbonate → HCID 54721818, Verbindung

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1(C)C=CC=CC=1.CCO.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[C:16]4[C:15]([OH:17])=[C:14]([C:18]#[N:19])[C:13](=[O:20])[NH:12][C:11]=4[S:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To an ambient slurry of 3-(4-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile (0.030 g, 0.086 mmol), 4-fluorophenyl boronic acid (0.024 g, 0.173 mmol) and cesium carbonate (0.084 g, 0.26 mmol) in DME/PhCH3/EtOH/H2O (10/1/6/3 ratio, 2 mL) was added palladium tetrakis(triphenylphosphine) (0.001 g, 0.0009 mmol) in a single portion. The reaction was heated at 60° C. for 16 h, cooled to room temperature, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (DCI/NH3) m/e 362.2 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ ppm 12.51 (br s, 1H), 7.75 (dd, 2H), 7.64 (d, 2H), 7.52 (d, 2H), 7.31 (apparent t, 2H), 7.07 (s, 1H).

Aufarbeitung

temperaturecooled to room temperature
filtrationfiltered
concentrationconcentrated
custompurified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag: ord-fbb729ddf842435b9ec60488e065ccd0
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07119205B2

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