Reaktion #162759

ord-b77fbc78aea049efbe40ef84e64179be

Reaktionsgleichung

Cc1ccc(B(O)O)cc1
4-tolylboronic acid
O=[N+]([O-])c1cn[nH]c1
4-nitropyrazole
c1ccncc1
pyridine
Cc1ccc(-n2cc([N+](=O)[O-])cn2)cc1
title compound
Ausbeute 31.0%
Cc1ccc(-n2cc([N+](=O)[O-])cn2)cc1
4-Nitro-1-p-tolyl-1H-pyrazole
Ausbeute 31.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was filtered through Celite
  2. 2
    Waschenwashing with DCM
  3. 3
    Sonstigeevaporated to dryness
  4. 4
    SonstigeThe residue was purified by FCC
  5. 5
    Wascheneluting with 0-30% ethyl acetate in cyclohexane

Vorschrift

To 4-tolylboronic acid (544 mg, 4.00 mmol), 4-nitropyrazole (226 mg, 2.00 mmol), copper (II) acetate (545 mg, 3.00 mmol), and 4 Å sieves (1.5 g) in DCM (15 mL), was added pyridine (0.32 mL, 4 mmol) at RT, and stirred for 5 h. The mixture was filtered through Celite, washing with DCM, then evaporated to dryness. The residue was purified by FCC, eluting with 0-30% ethyl acetate in cyclohexane, to give the title compound as a white solid (126 mg, 31%). LCMS (Method 3): Rt 3.93 min, m/z 204.1 [MH−].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08835431B2uspto-grants-2014_09