Diisopropylethylamine → HCID 52933726, Verbindung

HRID 2075692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075692
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:13][N:14]=[C:7]1[CH:6]=[CH:5]2.CCN(C(C)C)C(C)C.[SH:30][C:31]1[CH:32]=[C:33]([C:37]2([OH:43])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1.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]>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:12]1[N:8]2[C:9]3[C:4]([CH:5]=[CH:6][C:7]2=[N:14][N:13]=1)=[CH:3][C:2]([S:30][C:31]1[CH:32]=[C:33]([C:37]2([OH:43])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1)=[CH:11][CH:10]=3

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58257801HCID 58257801, VerbindungHCID 670909637-Iodo-1-pyridin-2-yl-[1,2,4]triazolo[4,3-a]quinoline

Produkt 1

HCID 52933726HCID 52933726, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

5k (201 mg, 0.54 mmol) was suspended in 1,4-dioxane (4.5 mL) and degassed with N2 for 5 minutes. iPr2NEt (0.19 mL, 1.08 mmol) was added, followed by 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-ol (51, 131 mg, 0.60 mmol) in 1,4-dioxane (1 mL). Pd2dba3 (13 mg, 0.01 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (16 mg, 0.03 mmol) were added, and the reaction was sealed and heated to 90° C. overnight. After cooling to room temperature, the mixture was concentrated and purified by silica gel chromatography (20-100% EtOAc in hexanes, followed by 0-10% MeOH in EtOAc) to obtain the desired product, 5p. Further purification by preparative HPLC was required, followed by standard aqueous workup of the combined fractions using EtOAc and saturated aqueous NaHCO3 to give clean product.

Aufarbeitung

  1. customdegassed with N2 for 5 minutes
  2. customthe reaction was sealed
  3. temperatureAfter cooling to room temperature
  4. concentrationthe mixture was concentrated
  5. custompurified by silica gel chromatography (20-100% EtOAc in hexanes, followed by 0-10% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-73c2ee4dd29f4d3ba727724f6a6126be
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919621B2

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