Toluene → 2-(Trimethylsilyl)ethyl [4-[2-(tetrahydro-2H-pyran-4-yloxy)ethoxy]phenyl}isoquinoline-6-carboxylate

HRID 1959948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959948
C1(C)C=CC=CC=1.FC(F)(F)S(O[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])[CH:22]=2)[CH:17]=[N:16][CH:15]=1)(=O)=O.CC1(C)C(C)(C)OB([C:43]2[CH:58]=[CH:57][C:46]([O:47][CH2:48][CH2:49][O:50][CH:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[CH:45][CH:44]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[O:54]1[CH2:53][CH2:52][CH:51]([O:50][CH2:49][CH2:48][O:47][C:46]2[CH:57]=[CH:58][C:43]([C:17]3[C:18]4[C:23](=[CH:22][C:21]([C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])=[CH:20][CH:19]=4)[CH:14]=[CH:15][N:16]=3)=[CH:44][CH:45]=2)[CH2:56][CH2:55]1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylateHCID 66730495HCID 66730495, Verbindung

Produkt 1

HCID 866619652-(Trimethylsilyl)ethyl [4-[2-(tetrahydro-2H-pyran-4-yloxy)ethoxy]phenyl}isoquinoline-6-carboxylateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Into toluene (10 ml), 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate (500 mg, 1.2 mmol) was dissolved, to which 4-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethoxy}tetrahydro-2H-pyran (630 mg, 1.8 mmol) synthesized in Reference Example 2, 4,5-bis(diphenylphosphino)-9-dimethylxanthene (210 mg, 0.36 mmol), tris(dibenzylideneacetone)palladium (160 mg, 0.17 mmol), and potassium carbonate (500 mg, 3.6 mmol) were added. The resulting mixture was stirred at 100° C. for four hours, to which ethyl acetate was added. The resulting mixture was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V) to give the desired title compound (307 mg, yield 52%).

Aufarbeitung

  1. additionwere added
  2. additionwas added
  3. washThe resulting mixture was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-39e40db86bff4dc19714de8e1c47b308
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410273B2

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