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2-Bromopyridine → HCID 178479691, Verbindung

HRID 658114
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 658114
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

A 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-9b01660c338a4d9484446a002dd20b07
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08076367B2

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