Triethylamine → 5-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1883627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883627
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[CH2:7][N:8]1[C:12]([CH:13]([F:15])[F:14])=[N:11][N:10]([CH3:16])[C:9]1=[O:17].C[C:21]([O:25][CH3:26])(C)[C:22]#[CH:23].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:28]=1.C(N(CC)CC)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)I.COC(C)(C)C.C(#N)C>[F:14][CH:13]([F:15])[C:12]1[N:8]([CH2:7][C:6]2[CH:18]=[C:2]([C:27]#[C:28][CH:22]([CH3:23])[CH2:21][O:25][CH3:26])[CH:3]=[CH:4][C:5]=2[CH3:19])[C:9](=[O:17])[N:10]([CH3:16])[N:11]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 49132563-Methoxy-3-methylbut-1-yneHCID 129940064-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one2×

Produkt 1

HCID 1317244995-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneAusbeute 686,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

498 mg (1.5 mmol) of 4-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 40), 378 mg (1.2 mmol) of 3-methyl-3-methoxy-1-butine, 21.1 mg (0.030 mmol) of PdCl2(PPh3)2, 19.0 mg (0.050 mmol) of copper iodide, 39.3 mg (0.15 mmol) of triphenylphosphine, 607 mg of triethylamine and 6.0 ml of acetonitrile were mixed, and the mixture was heated under reflux for 4.5 hours in nitrogen atmosphere. After cooling to room temperature, t-butyl methyl ether was added to the reaction solution, and the mixture was filtrated through celite, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=2/1 (v/v)) to obtain 360 mg of 5-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 326).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hours in nitrogen atmosphere
  3. filtrationthe mixture was filtrated through celite
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f3c8c7914d304070ac449f90d25c0cec
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762197B2

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