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Potassium Phosphate, Tribasic → HCID 178469763, Verbindung

HRID 593702
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593702
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[C:5](Cl)=[N:4][N:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:37]=2)[C:32]([O:34][CH2:35][CH3:36])=[O:33])O1.[O-:39]P([O-])([O-])=O.[K+].[K+].[K+].F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.O.C([O-])=O.[NH4+].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]>[OH:39][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([CH:37]=2)[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N:3][N:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 3816953Ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylateHCID 11710396Tricyclohexylphosphonium TetrafluoroborateHCID 904244121,4-Dichloro-5-phenylphthalazine

Produkt 1

HCID 178469763HCID 178469763, VerbindungAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 2723923Ammonium formateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 1,4-dichloro-5-phenylphthalazine (5.00 g, 18.2 mmol) in 1,4-dioxane (50 mL) and water (9 mL) was added ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (5.32 g, 27.3 mmol), and K3PO4 (7.72 g, 36.3 mmol). The contents were purged with nitrogen for 10 min. Tricyclohexylphosphonium tetrafluoroborate (0.402 g, 1.09 mmol) was added followed by Pd2(dba)3 (0.416 g, 0.454 mmol) and the reaction mixture was heated at 95° C. for 12 h. The reaction mixture was allowed to cool to ambient temperature and diluted with HCOONH4 buffer (pH˜5) solution. The reaction mixture was extracted with EtOAc (3×75 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with EtOAc to afford ethyl 5-(4-hydroxy-5-phenylphthalazin-1-yl)nicotinate (3.50 g, 44.1%) as an off-white solid which is 85% pure by LC-MS. LCMS (Condition 1): retention time 2.52 min, [M+1]=372.0. 1H NMR (400 MHz, DMSO-d6) δ 1.37 (t, J=7.2 Hz, 3 H), 4.41 (q, J=7.2 Hz, 2 H), 7.33-7.42 (m, 5 H), 7.62-7.65 (m, 2 H), 7.92 (dd, J=7.6 Hz, J=8.0 Hz, 1 H), 8.49 (t, J=2.0 Hz, 1 H), 9.07 (d, J=2.0 Hz, 1 H), 9.25 (d, J=2.0 Hz, 1 H), 12.74 (br s, 1 H).

Aufarbeitung

  1. customThe contents were purged with nitrogen for 10 min
  2. temperatureto cool to ambient temperature
  3. extractionThe reaction mixture was extracted with EtOAc (3×75 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b159a69123c8400baa6d818e58940d52
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242966B2

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