Pyridine → 4-Nitro-1-p-tolyl-1H-pyrazole

HRID 75577

Reaktionsgleichung

Reaktionsgleichung von HRID 75577
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.[N+:11]([C:14]1[CH:15]=[N:16][NH:17][CH:18]=1)([O-:13])=[O:12].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N+:11]([C:14]1[CH:15]=[N:16][N:17]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[CH:18]=1)([O-:13])=[O:12]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 163764-nitro-1H-pyrazoleHCID 79799Tolylboronic acid

Produkt 1

HCID 114130304-Nitro-1-p-tolyl-1H-pyrazoleAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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−].

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washwashing with DCM
  3. customevaporated to dryness
  4. customThe residue was purified by FCC
  5. washeluting with 0-30% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-b77fbc78aea049efbe40ef84e64179be
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835431B2

Verknüpfte Notizen

Wird geladen…