Potassium Carbonate → N-cyclopropyl-3-(1-(2,4-dimethylphenyl)phthalazin-6-yl)-4-methylbenzamide

HRID 2357561

Reaktionsgleichung

Reaktionsgleichung von HRID 2357561
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19])=[N:7][N:6]=[CH:5]2.[CH:20]1([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27](B3OC(C)(C)C(C)(C)O3)[CH:26]=2)[CH2:22][CH2:21]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:20]1([NH:23][C:24](=[O:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=3[CH3:19])=[N:7][N:6]=[CH:5]4)[CH:26]=2)[CH2:21][CH2:22]1

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 27349382-(Dicyclohexylphosphino)-2'-methylbiphenylHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 68454866HCID 68454866, Verbindung

Produkt 1

HCID 68452425N-cyclopropyl-3-(1-(2,4-dimethylphenyl)phthalazin-6-yl)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-1-(2,4-dimethylphenyl)phthalazine (150 mg, 558 μmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (437 mg, 1450 μmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (18.3 mg, 50.2 μmol, Strem), Pd2(dba)3 (15.3 mg, 16.7 μmol, Strem), and potassium carbonate (231 mg, 1674 μmol) in Dioxane:H2O=4:1 (5 mL) was heated to 80° C. for 18 h. After cooling to room temperature, the mixture was diluted with MeOH and concentrated over SiO2. The residue was purified with column chromatography (MeOH/CH2Cl2=0-4%). The residue was purified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 mL/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient). Yield: 113 mg (50%). MS (ESI, pos. ion) m/z: 408 (M+1).

Aufarbeitung

  1. concentrationconcentrated over SiO2
  2. customThe residue was purified with column chromatography (MeOH/CH2Cl2=0-4%)
  3. customThe residue was purified with reverse-phase chromatography (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 mL/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 min gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0a582763ec8c4a5d9a829294ca033bc5
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759337B2

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