Acetonitrile → 3-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1876870

Reaktionsgleichung

Reaktionsgleichung von HRID 1876870
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C(#N)C.[CH:18]1(/[CH:21]=[CH:22]/[C:23]#[N:24])[CH2:20][CH2:19]1.N12CCCN=C1CCCCC2>>[CH:18]1([CH:21]([N:12]2[CH:13]=[C:9]([B:4]3[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]3)[CH:10]=[N:11]2)[CH2:22][C:23]#[N:24])[CH2:20][CH2:19]1

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 594201403-Cyclopropylprop-2-enenitrile

Produkt 1

HCID 674580563-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

Versuchsvorschrift

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (10.0 g, 0.0515 mol) in acetonitrile (129 mL, 2.46 mol) was added (E)-3-cyclopropylacrylonitrile (5.75 g, 0.0617 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (3.85 mL, 0.0258 mol). The resulting mixture was stirred at room temperature overnight, and evaporated to dryness. The mixture was purified on silica gel, eluting with 0 to 80% EtOAc in hexanes, to give the desired product as racemic mixture (10.8 g, 73.0%). LCMS (M+H) 288.4.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe mixture was purified on silica gel
  3. washeluting with 0 to 80% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-259763eb655f40b4a22e1fa06d17cb34
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309718B2

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