Potassium Phosphate, Tribasic → 2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile

HRID 1028958

Reaktionsgleichung

Reaktionsgleichung von HRID 1028958
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:44]1[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][C:45]=1[C:46]#[N:47].[O:53]1[CH2:58][CH2:57][N:56]([C:59]2[C:60]([NH2:78])=[N:61][C:62]3[C:67]([CH:68]=2)=[CH:66][C:65](B2OC(C)(C)C(C)(C)O2)=[CH:64][CH:63]=3)[CH2:55][CH2:54]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[NH2:78][C:60]1[C:59]([N:56]2[CH2:57][CH2:58][O:53][CH2:54][CH2:55]2)=[CH:68][C:67]2[C:62](=[CH:63][CH:64]=[C:65]([C:44]3[C:51]([CH3:52])=[CH:50][CH:49]=[CH:48][C:45]=3[C:46]#[N:47])[CH:66]=2)[N:61]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 154691152-Bromo-3-methylbenzonitrileHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

Produkt 1

HCID 673450552-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a mixture of potassium phosphate (5.98 g, 28.2 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.54 g, 1.13 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), 2-bromo-3-methylbenzonitrile (2.21 g, 11.26 mmol) and 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (2.00 g, 5.63 mmol, prepared as in Example 2, Step 1-2) was added dioxane (50.0 mL) and water (25.0 mL). The mixture was heated to 140° C. for 10 min. The reaction mixture was allowed to cool to RT, filtered and then partitioned between EtOAc and water. The organic layer was washed with water and brine, and concentrated. The residue was diluted with EtOAc and then filtered. The solid was dried in air to afford 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile as a light brown solid.

Aufarbeitung

  1. temperatureto cool to RT
  2. filtrationfiltered
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with water and brine
  5. concentrationconcentrated
  6. additionThe residue was diluted with EtOAc
  7. filtrationfiltered
  8. customThe solid was dried in air

Quellen und Nachweise

ORD-Eintrag
ord-7f6f23c9a4ae497b955691427325cfcf
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735384B2

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