Ammonium Chloride → HCID 21106569, Verbindung

HRID 1783669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783669
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:17]([CH3:19])[CH3:18])[C:9]2=[O:20])=O)C.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)[C:9](=[O:20])[N:10]([CH:17]([CH3:19])[CH3:18])[N:11]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 68898772Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester

Produkt 1

HCID 21106569HCID 21106569, VerbindungAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and DCM (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 8.28 (1H, s), 7.96 (1H, d), 7.88 (1 H, d), 5.64 (1H, t), 5.31-5.18 (1H, m), 4.78 (2H, d), 1.35 (6H, d); MS (ESI+)=(M+H)+ 297 & 299

Aufarbeitung

  1. temperatureto warm to RT
  2. stirringwas stirred for a further 3 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customthe reaction mixture was then partitioned between water (50 ml) and DCM (150 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM)

Quellen und Nachweise

ORD-Eintrag
ord-866127e293914165a8ab8b3a807a9b0f
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501410B2

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