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2-Bromopyridine → HCID 178479691, Verbindung

HRID 2233788
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2233788
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[C:22]([C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34])[C:23]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH:28]=[O:29])=[O:24].[Cl-:42].[NH4+]>C1COCC1>[ClH:42].[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[C:22]([C:23]([C:25]1[CH:32]=[CH:31][CH:30]=[C:27]([CH:28]([OH:29])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:26]=1)=[O:24])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178519574HCID 178519574, Verbindung

Produkt 1

HCID 178479691HCID 178479691, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

0.33 ml portion of 2-bromopyridine was dissolved in 3 ml of THF, and the solution was cooled to −78° C., mixed with 2.2 ml of n-butyl lithium and then stirred at the same temperature for 30 minutes. This solution was poured at −78° C. into a solution prepared by dissolving 3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]benzaldehyde in 10 ml of THF. This was slowly risen to room temperature and mixed with 50 ml of saturated ammonium chloride aqueous solution. This was extracted with ethyl acetate, dried with sodium sulfate and then concentrated, and the thus formed residue was purified by a silica gel column chromatography (chloroform:methanol=from 100:0 to 90:10). By subjecting the thus obtained reddish brown solid to salt formation with 4N HCl/EtOAC (0.2 ml), 151 mg (42%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-{3-[hydroxy(pyridin-2-yl)methyl]phenyl}propane-1,3-dione hydrochloride (Example 11-1) was obtained. FA: 466

Aufarbeitung

  1. additionThis solution was poured at −78° C. into a solution
  2. customprepared
  3. customThis was slowly risen to room temperature
  4. extractionThis was extracted with ethyl acetate
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customthe thus formed residue was purified by a silica gel column chromatography (chloroform:methanol=from 100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-d4fbc71ea09f4695a1e4125f852e8cfc
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709519B2

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