2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 66584619, Verbindung

HRID 2369015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369015
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][C:34]([F:38])=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[CH:39](B1OC(C)(C)C(C)(C)O1)=[CH2:40]>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:38][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][C:28]([C:27]1[CH:26]=[N:25][N:5]3[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:2]([CH:39]=[CH2:40])=[N:3][C:4]=13)=[CH:37]2

Komponenten

6

Edukt 2

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86686735HCID 86686735, Verbindung

Produkt 1

HCID 66584619HCID 66584619, VerbindungAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 10340Sodium CarbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 5-chloro-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (2.5 g, 4.4 mmol) in 1,4-Dioxane (50 mL) and 2M Na2CO3 (25 mL) was added vinylboronic acid pinacol ester (0.9 ml, 5.2 mmol), and Pd(PPh3)4 (0.5 g, 0.4 mmol). The reaction mixture was heated at 100° C. for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. Following removal of dioxane under reduced pressure, organics were extracted with CH2Cl2 (4×40 mL, dried (Na2SO4) and concentrated in vacuo. Gradient column chromatography on silica eluting with 20 to 50% EtOAc/hexanes gave 3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5-vinylpyrazolo[1,5-a]pyrimidin-7-amine as a yellow solid (2.2 g, 3.89 mmol, 88%). LC/MS: 3.05 mins, m/z=566.3 (MH+).

Aufarbeitung

  1. customconsumption of starting material
  2. customremoval of dioxane under reduced pressure
  3. extractionorganics were extracted with CH2Cl2 (4×40 mL
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d54ee2e3ef294b83bc61688c13453925
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703784B2

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