HCID 10270183, Verbindung → HCID 10114380, Verbindung

HRID 2250994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250994
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[CH:17]=[C:16]([NH:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[N:15]=[C:14]([CH3:24])[N:13]=1)[CH2:6][CH2:5]2.[Br-:25].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:25][C:17]1[C:12]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[Cl:11])[CH2:5][CH2:6]2)=[N:13][C:14]([CH3:24])=[N:15][C:16]=1[NH:18][CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21]

Komponenten

4

Edukt 2

HCID 10270183HCID 10270183, VerbindungHCID 21124087Pyridiniumtribromide

Produkt 1

HCID 10114380HCID 10114380, VerbindungAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.15 g, 3.14 mmol) and pyridinium tribromide (1.16 g, 3.63 mmol) were stirred in dry dichloromethane (20 mL) at 20° C. for 16 h. The reaction mixture was quenched with saturated aqueous Na2S2O5 (6 mL) and diluted with EtOAc (200 mL). The EtOAc was washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes to give the product, 5-bromo-4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.30 g, 93% yield).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated aqueous Na2S2O5 (6 mL)
  2. additiondiluted with EtOAc (200 mL)
  3. washThe EtOAc was washed with water, brine
  4. customdried
  5. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-11224d5736ec4766a0a9a3468a70eda8
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319100B2

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