Binap, (A+-)- → HCID 24946519, Verbindung

HRID 1803523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803523
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].[N:14]1([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH2:22][NH2:23])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>CC(N(C)C)=O.CCOC(C)=O.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]>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:23][CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 634876Binap, (A+-)-HCID 27765092-PIPERIDINOBENZYLAMINEHCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Produkt 1

HCID 24946519HCID 24946519, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2-piperidin-1-yl-benzylamine (122 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (108 mg, 0.17 mmol) and NaOt-Bu (251 mg, 2.61 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2-piperidin-1-yl-benzylamino)-2H-phthalazin-1-one: 62 mg (29.0%): m/z (M+H)=369. 1H-NMR (DMSO-d6) δ: 12.35 (s, 1H), 7.90 (d, 1H), 7.77 (m, 1H), 7.32 (dd, 1H), 7.15 (m, 3H), 6.96 (m, 1H) 6.62 (s, 1H), 4.41 (d, 2H), 1.71 (m, 4H), 1.55 (m, 2H).

Aufarbeitung

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09d42394f3784c199c4a8974420938d9
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349836B2

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