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Diisopropylethylamine → 4-[3-(2-Oxo-1,2-dihydro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075687
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Reaktionsgleichung

Reaktionsgleichung von HRID 2075687
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[SH:13][C:14]1[CH:15]=[C:16]([C:20]2([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1.CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:12]=[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:17]=[CH:18][CH:19]=3)[CH:3]=2)[NH:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 138361846-Iodoquinolin-2(1H)-oneHCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile

Produkt 1

HCID 589265284-[3-(2-Oxo-1,2-dihydro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-Iodo-1H-quinolin-2-one (5.13 g, 18.9 mmol) and 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (5f, 4.57 g, 20.8 mmol) were dissolved in 1,4-dioxane (160 mL) and degassed for 10 minutes with N2. iPr2NEt (6.6 mL, 37.9 mmol) was added, followed by Pd2dba3 (434 mg, 0.47 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (548 mg, 0.95 mmol), and the reaction was degassed for another 10 minutes with N2. The reaction was then sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was filtered and concentrated, and the residue was purified by silica gel chromatography (0-100% MeOH in EtOAc) to give the desired product, 5g.

Aufarbeitung

  1. customdegassed for 10 minutes with N2
  2. customthe reaction was degassed for another 10 minutes with N2
  3. customThe reaction was then sealed
  4. temperatureAfter cooling to room temperature
  5. filtrationthe reaction was filtered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-100% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5341f1e6db8c42228d0c75e225a9e457
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07919621B2

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