Potassium Phosphate, Tribasic → 5-(4-(Trifluoromethyl)phenyl)pyridazin-3(2H)-one

HRID 2059875

Reaktionsgleichung

Reaktionsgleichung von HRID 2059875
C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.I[C:21]1[CH:26]=[N:25][NH:24][C:23](=[O:27])[CH:22]=1.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:28][C:29]([F:40])([F:39])[C:30]1[CH:35]=[CH:34][C:33]([C:21]2[CH:26]=[N:25][NH:24][C:23](=[O:27])[CH:22]=2)=[CH:32][CH:31]=1

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 166383305-Iodo-2,3-dihydropyridazin-3-one

Produkt 1

HCID 579503875-(4-(Trifluoromethyl)phenyl)pyridazin-3(2H)-oneAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Tricyclohexyl phosphine (16.6 μL, 0.02 mmol) was added to a mixture of 5-iodopyridazin-3(2H)-one (35 mg, 0.16 mmol), 4-(trifluoromethyl)phenylboronic acid (30 mg, 0.16 mmol), potassium phosphate tribasic (117 mg, 0.55 mmol), and palladium (II) acetate (3.5 mg, 0.02 mmol) in Toluene (0.8 mL) and Water (0.3 mL). The mixture was stirred at 100° C. for 22 hours. The reaction was diluted with CH2Cl2, filtered and concentrated. The crude was purified using HPLC (Phen Luna Axia C18 5μ 10:90:0.1 to 90:10:0.1 MeOH—H2O-TFA) to afford the desired product 5-(4-(trifluoromethyl)phenyl)pyridazin-3(2H)-one 18A (14.8 mg, 0.06 mmol, 39.1% yield) as a white solid. LC/MS 282 (M+H)+, tR 0.77 min (method 5).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude was purified

Quellen und Nachweise

ORD-Eintrag
ord-298cfe593174440d8b9f2ab3d35484b9
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278316B2

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