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Ethyl Acetate → HCID 66855693, Verbindung

HRID 1530100
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530100
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:12]3[S:13][C:14]([C:23]4[N:27]=[CH:26][N:25]([CH:28]5[CH2:33][CH2:32][CH2:31][CH2:30][O:29]5)[N:24]=4)=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:16]=3)=[C:9]([CH3:11])[N:10]=2)[CH:7]=1.[CH3:34][N:35]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[N:36]1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>COCCOC.O>[CH3:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([C:38]3[CH:37]=[N:36][N:35]([CH3:34])[CH:39]=3)=[CH:7][N:6]2[C:8]=1[C:12]1[S:13][C:14]([C:23]2[N:27]=[CH:26][N:25]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[N:24]=2)=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58094803HCID 58094803, Verbindung

Produkt 1

HCID 66855693HCID 66855693, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a suspension of 6-bromo-2-methyl-3-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl}-1,3-thiazol-2-yl]imidazo[1,2-a]pyridine (157 mg, 0.3 mmol) obtained in Example 117-B(i) in DME (10 mL) and water (2 mL), were added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (93.6 mg, 0.45 mmol), [1,1-bis(diphenylphosphino)ferrocene]palladium(II)dichloride dichloromethane complex (24.5 mg, 0.03 mmol) and cesium carbonate (293 mg, 0.9 mmol) under a nitrogen atmosphere, and the mixture was stirred at 95° C. for 12 h. The reaction mixture was allowed to cool to rt, and then were added water (40 mL) and EtOAc (40 mL). The aqueous layer was extracted with EtOAc (40 mL) and then a 1:1 mixture of EtOAc and THF (60 mL×2), and the combined organic layers were dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was washed with THF to give the title compound (64.0 mg, 41%) as a white solid.

Aufarbeitung

  1. temperatureto cool to rt
  2. extractionThe aqueous layer was extracted with EtOAc (40 mL)
  3. additiona 1:1 mixture of EtOAc and THF (60 mL×2)
  4. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  5. customInsoluble materials were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe residue was washed with THF

Quellen und Nachweise

ORD-Eintrag
ord-fb26bb3249634c5b8eb0a8f1363e1a80
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090601B2

Notizen zur Reaktion

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