Potassium Carbonate → 1-phenyl-4-(thiophen-2-yl)-1H-pyrazole

HRID 705008

Reaktionsgleichung

Reaktionsgleichung von HRID 705008
Br[C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1(C)C(CO)=CC=CC=1>[C:7]1([N:5]2[CH:6]=[C:2]([C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[CH:3]=[N:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 7868114-Bromo-1-phenyl-1H-pyrazoleHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 863036571-phenyl-4-(thiophen-2-yl)-1H-pyrazoleAusbeute 27,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 69942-Methylbenzyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Bromo-1-phenyl-1H-pyrazole (150 mg, 0.672 mmol), thiophen-2-ylboronic acid (296 mg, 2.31 mmol), PEPPSI-iPr (13.6 mg, 0.062 mmol), and K2CO3 (480 mg, 3.48 mmol) were combined in toluene-methanol (1:1) (2 ml). The reaction mixture was heated under microwave at 80° C. for 10 minutes. The reaction mixture was then filtered and washed with toluene-methanol (5 ml), and the filtrate was concentrated. The crude mixture was then column purified using 15-20% ethyl acetate/hexane to yield 1-phenyl-4-(thiophen-2-yl)-1H-pyrazole (42 mg, yield 27%). The HPLC purity of the final product was 99.32%. LC-MS [M+H] 227 (C13H10N2S+H expected 227.06). The 1H-NMR spectra was in accordance with the chemical structure.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. washwashed with toluene-methanol (5 ml)
  3. concentrationthe filtrate was concentrated
  4. customcolumn purified

Quellen und Nachweise

ORD-Eintrag
ord-a8ce2f9bd9874f59a0cb959843098fe4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173401B2

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