Dimethylacetamide → HCID 24946166, Verbindung

HRID 1803532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1803532
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.[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24](NC)[C:19]=2[O:18][CH2:17][CH2:16]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+].C[C:80]([N:82](C)C)=O>CCOC(C)=O>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:82][CH2:80][C:24]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:20]=4[CH:21]=[CH:22][CH:23]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Komponenten

7

Edukt 5

HCID 31374DimethylacetamideHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 67417056HCID 67417056, Verbindung

Produkt 1

HCID 24946166HCID 24946166, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), (2,3-dihydro-benzo[1,4]dioxin-5-yl)-methylamine hydrochloride (129 mg, 0.64 mmol), Pd-2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 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-[(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-amino]-2H-phthalazin-1-one: 41 mg (20.6%): m/z (M+H)=344. 1H-NMR (DMSO-d6) δ: 12.33 (s, 1H), 7.92 (d, 1H), 7.53 (m, 1H), 7.13 (dd, 1H), 6.82 (m, 4H), 4.33 (m, 4H), 4.26 (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-e09a738d1a014e329579d024d4f300ed
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349836B2

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