Benzenemethanamine, 3,5-dichloro- → 4-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one

HRID 1803556

Reaktionsgleichung

Reaktionsgleichung von HRID 1803556
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].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[CH2:18][NH2:19].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:19][CH2:18][C:17]3[CH:16]=[C:15]([Cl:14])[CH:22]=[C:21]([Cl:23])[CH:20]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 457602Benzenemethanamine, 3,5-dichloro-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Produkt 1

HCID 249485344-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-oneAusbeute 2,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (97 mg, 0.374 mmol), 3,5-dichlorobenzylamine (0.057 mL, 0.424 mmol), Pd2(dba)3 (29 mg, 0.032 mmol), rac-BINAP (70 mg, 0.112 mmol) and NaOtBu (104 mg, 1.08 mmol) in DMA (5 mL) was heated at 80° C. for 1.5 h. The mixture was allowed to cool, diluted with EtOAc and washed with water. The organic layer was washed with sat.aq. NaHCO3, brine and dried (Na2SO4). Chromatography on silica (EtOAc/hexanes) afforded 4-chloro-6-(3,5-dichloro-benzylamino)-2H-phthalazin-1-one (3 mg) as a white solid, 1H (400 MHz, CDCl3) δ: 4.40 (s, 2H), 6.84 (m, 1H), 6.99 (m, 1H), 7.22 (m, 3H), 8.14 (m, 1H), 10.80 (s, 1H) ppm; m/z (M+1) 353.83.

Aufarbeitung

  1. temperatureto cool
  2. washwashed with water
  3. washThe organic layer was washed with sat.aq
  4. dry with materialNaHCO3, brine and dried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-e5414037facb43e5aecd795d788d6366
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349836B2

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