2,5-Dimethoxybenzenemethanamine → 4-chloro-6-(2,5-dimethoxy-benzylamino)-2H-phthalazin-1-one

HRID 1667483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667483
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].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:17]=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:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:16]=3[O:15][CH3:14])[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 186522,5-DimethoxybenzenemethanamineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-one

Produkt 1

HCID 249483404-chloro-6-(2,5-dimethoxy-benzylamino)-2H-phthalazin-1-oneAusbeute 17,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (155 mg, 0.597 mmol), 2,5-dimethoxybenzylamine (0.096 mL, 0.636 mmol), Pd2(dba)3 (61 mg, 0.067 mmol), rac-BINAP (111 mg, 0.178 mmol) and NaOtBu (139 mg, 1.445 mmol) in DMA (5 mL) was heated at 85° 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-(2,5-dimethoxy-benzylamino)-2H-phthalazin-1-one (37 mg) as an off white solid, 1H (400 MHz, d6-DMSO) δ: 3.45 (s, 3H), 3.61 (s, 3H), 4.17 (d, 2H), 6.63 (m, 3H), 6.76 (d, 1H), 6.94 (dd, 1H), 7.33 (t, 1H), 7.72 (d, 1H), 12.14 (s, 1H) ppm; m/z (M+1) 345.92.

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-4701e32c7ebd4fb98a15a126c1f141a0
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044041B2

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