Acetonitrile → 4-(2,4-Dimethoxy-3-nitro-phenylethynyl)-1-methyl-1H-pyrazole

HRID 2059612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059612
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([O:12][CH3:13])[CH:6]=[CH:5][C:4]=1I.[C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1)#[CH:16].C(#N)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[C:7]([O:12][CH3:13])[CH:6]=[CH:5][C:4]=1[C:16]#[C:15][C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1

Komponenten

7

Edukt 3

HCID 6342AcetonitrileHCID 511383214-Ethynyl-1-methyl-1H-pyrazoleHCID 574219462,4-Dimethoxy-3-nitro-iodobenzene

Produkt 1

HCID 687741874-(2,4-Dimethoxy-3-nitro-phenylethynyl)-1-methyl-1H-pyrazoleAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 2,4-dimethoxy-3-nitro-iodobenzene (0.95 mmol), 0.122 g (1.15 mmol) of 4-ethynyl-1-methyl-1H-pyrazole, 0.028 g (0.04 mmol) of dichlorobis (triphenylphosphine)palladium (H) and 8 mg (0.042 mmol) of copper (I) iodide 4 mL of anhydrous acetonitrile and 2 mL of triethylamine were added under nitrogen atmosphere at room temperature. The resulting mixture was stirred for 1 hour, when TLC indicated a consumption of the iodobenzene. The solvent was evaporated under reduced pressure and the residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1) to give the title compound in 71% yield as creamy crystals. H1 NMR (CDCl3) 3.88(s, 3H, Me); 3.9 (s, 3H, OMe); 4.07 (s, 3H, OMe); 6.7 (d, 1H, CH, J=8.9 Hz); 7.44 (d, 1H, CH, J=8.9 Hz); 7.56 (s, 1H, CH pyr); 7.62 (s, 1H, CH pyr).

Aufarbeitung

  1. additionwere added under nitrogen atmosphere at room temperature
  2. customa consumption of the iodobenzene
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b97c8df0a304ae1a3a6be24f0a12dcc
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278290B2

Notizen zur Reaktion

Wird geladen…