4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide → (4-bromo-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanone

HRID 2401436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2401436
[Br:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>O1CCCC1>[Br:1][C:2]1[C:3]([C:8]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)=[O:9])=[N:4][N:5]([CH3:7])[CH:6]=1

Komponenten

4

Edukt 2

HCID 866667294-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamideHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 67818210(4-bromo-1-methyl-1H-pyrazol-3-yl)(4-chlorophenyl)methanoneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of compound 4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide (1.0 g, 4 mmol) in anhydrous tetrahydrofuran (20 mL) under nitrogen atmosphere was added (4-chlorophenyl)magnesium bromide (8 mL) in tetrahydrofuran (1 M) at 0° C., The resulting mixture was stirred for 2 h at room temperature. The reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL) was added, the separated organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum. The residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=5:1 to give the titled product as a white solid (1.0 g, 84%). LC/MS m/z 298 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=9 Hz, 2H), 7.53 (s, 1H), 7.43 (d, J=9 Hz, 2H), 3.99 (s, 3H).

Aufarbeitung

  1. customThe reaction was quenched by saturated solution of ammonium chloride, and dichloromethane (100 mL)
  2. additionwas added
  3. dry with materialthe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography
  6. washeluting with petroleum ether/ethyl acetate=5:1

Quellen und Nachweise

ORD-Eintrag
ord-c71cac47280541ba980084ca1daa03fb
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796261B2

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