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Triphenylphosphine → HCID 59321556, Verbindung

HRID 2423530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2423530
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:7][CH:6]=[CH:5]2.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[C:25]1[C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)=[C:28]([CH:47]([CH3:49])[CH3:48])[O:27][N:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.O1CCOCC1>[Cl:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[C:19]=1[C:25]1[C:29]([CH2:30][O:31][C:32]2[CH:33]=[CH:34][C:35]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:7][CH:6]=[CH:5]4)=[CH:36][CH:37]=2)=[C:28]([CH:47]([CH3:49])[CH3:48])[O:27][N:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 59321519Ethyl 6-bromoisoquinoline-1-carboxylateHCID 597090393-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole

Produkt 1

HCID 59321556HCID 59321556, Verbindung
Ausbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Palladium(II)acetate (2.5 mg, 11.2 μmol) was added to ethyl 6-bromo-1-isoquinolinecarboxylate (62.7 mg, 223.8 μmol), 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-({[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}methyl)isoxazole (109.3 mg, 223.8 μmol), triphenylphosphine (5.9 mg, 22.4 μmol), and potassium phosphate (166.3 mg, 783.4 μmol). Then, dioxane (2.2 mL) was added to the mixture, followed by water (22.4 μL), and the reaction mixture was heated open to the atmosphere at 60° C. in an oil bath for 67 hours, then allowed to cool to room temperature. Water was added, followed by ethyl acetate, and the mixture was filtered through Celite®. The filtrate was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 2:3 ethyl acetate:hexanes to give 53.6 mg (43%) of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-isoquinolinecarboxylate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 8.56 (d, J=5 Hz, 1H), 8.47 (d, J=9 Hz, 1H), 8.30 (s, 1H), 8.08-8.03 (m, 2H), 7.75 (d, J=9 Hz, 2H), 7.65-7.60 (m, 2H), 7.55 (dd, J=9, 7 Hz, 1H), 6.95 (d, J=9 Hz, 2H), 4.90 (s, 2H), 4.47 (q, J=7 Hz, 2H), 3.48 (septet, J=7 Hz, 1H), 1.38 (t, J=7 Hz, 3H), 1.34 (d, J=7 Hz, 6H). ESI-LCMS m/z 560 (M+H)+.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through Celite®
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 2:3 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b824448df0604140acb975ffff5e0eb8
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960552B2

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