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Potassium Carbonate → Methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate

HRID 2423395
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2423395
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl[CH2:60][C:61]1[C:62]([C:69]2[C:74]([Cl:75])=[CH:73][CH:72]=[CH:71][C:70]=2[Cl:76])=[N:63][O:64][C:65]=1[CH:66]([CH3:68])[CH3:67].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CN(C=O)C.O>[Cl:75][C:74]1[CH:73]=[CH:72][CH:71]=[C:70]([Cl:76])[C:69]=1[C:62]1[C:61]([CH2:60][O:30][C:27]2[CH:26]=[CH:25][C:24]([C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:8]=[N:9]4)=[CH:4][CH:3]=3)=[CH:29][CH:28]=2)=[C:65]([CH:66]([CH3:68])[CH3:67])[O:64][N:63]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

12

Edukt 6

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazoleHCID 59321547Methyl 7-bromoquinoline-3-carboxylate

Produkt 1

HCID 59321510Methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylateAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 78 mg (0.29 mmol) of methyl 7-bromo-3-quinolinecarboxylate, 97 mg (0.44 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 3 mg (0.01 mmol) of palladium acetate, 8 mg (0.03 mmol) of triphenylphosphine, 218 mg (1.03 mmol) of K3PO4 and 25 μL of H2O in 1.0 mL of dioxane was stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with water and brine then concentrated. To the residue was added 65 mg (0.21 mmol) of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole, 74 mg (0.54 mmol) of K2CO3 and 1.5 mL of DMF and the mixture was then stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with three portions of water, then brine. The solution was concentrated and the residue purified by silica gel chromatography (12 g of silica gel eluting with 0-40% EtOAc in hexanes over 45 minutes) to give 47 mg (30%) of methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate as a clear glass. 1H NMR (400 MHz, CDCl3): δ 9.44 (s, 1H), 8.83 (s, 1H), 8.28 (s, 1H), 7.96 (d, J=9 Hz, 1H), 7.82 (d, J=9 Hz, 1H), 7.64 (d, J=9 Hz, 2H), 7.41 (d, J=8 Hz, 2H), 7.35-7.31 (m, 1H), 6.92 (d, J=9 Hz, 2H), 4.79 (s, 2H), 4.02 (s, 3H), 3.38-3.34 (m, 1H), 1.45 (d, J=7 Hz, 6H). ESI-LCMS m/z 548 (M+H)+.

Aufarbeitung

  1. washthe organics were washed with water and brine
  2. concentrationthen concentrated
  3. washthe organics were washed with three portions of water
  4. concentrationThe solution was concentrated
  5. customthe residue purified by silica gel chromatography (12 g of silica gel eluting with 0-40% EtOAc in hexanes over 45 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-27ec22573b4c4f218385e03196a04c0a
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960552B2

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