Ethanol → Methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate

HRID 422557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422557
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.CC1(C)CC(C)OB([C:31](=[CH2:36])[C:32]([F:35])([F:34])[F:33])O1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:22][C:21]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([C:31](=[CH2:36])[C:32]([F:35])([F:34])[F:33])=[N:3][N:4]=[CH:5]2

Komponenten

8

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 164142704,4,6-Trimethyl-2-(3,3,3-trifluoroprop-1-en-2-yl)-1,3,2-dioxaborinaneHCID 77230175Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate

Produkt 1

HCID 66675460Methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoateAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (563 mg, 1800 μmol), 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (799 mg, 3600 μmol), tetrakis(triphenylphosphine)palladium (208 mg, 180 μmol), ethyl alcohol (200 proof; 2000 μl), 1,2-dimethoxyethane (8000 μl), and potassium carbonate (2M aqueous solution; 2700 μl, 5400 μmol) were combined in a sealed tube and heated at 80° C. for 2 h, during which LC-MS indicated 100% conversion. The cooled reaction was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 solution and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. CombiFlash purification (20% to 80% EtOAc/Hexanes) afforded methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate (210 mg, 31% yield) as a golden yellow foam. MS (ES+): 373.2 (M+H)+.

Aufarbeitung

  1. customThe cooled reaction
  2. washwashed with saturated aqueous NaHCO3 solution and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCombiFlash purification (20% to 80% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-26d7d9d5e9a647bf97cf573acc9d83eb
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101612B2

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