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Phosphorus oxychloride → 7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-carbaldehyde hydrochloride

HRID 1932362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1932362
P(Cl)(Cl)([Cl:3])=O.Cl.[F:7][C:8]1[CH:9]=[C:10]([CH:32]=[CH:33][CH:34]=1)[CH2:11][N:12]1[C:16]2=[C:17]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22]3)[N:18]=[CH:19][CH:20]=[C:15]2[CH:14]=[C:13]1[CH3:31].[C:35](=O)(O)[O-:36].[Na+]>CN(C)C=O>[ClH:3].[CH2:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:29][CH2:30][N:21]1[C:17]1[N:18]=[CH:19][CH:20]=[C:15]2[C:14]([CH:35]=[O:36])=[C:13]([CH3:31])[N:12]([CH2:11][C:10]3[CH:32]=[CH:33][CH:34]=[C:8]([F:7])[CH:9]=3)[C:16]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 67141928HCID 67141928, Verbindung

Produkt 1

HCID 866152557-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-carbaldehyde hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Phosphorus oxychloride (44 μl, 0.47 mmol) was added to a solution of 2-[1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline hydrochloride (115 mg, 0.31 mmol) prepared in Example 613 in N,N-dimethylformamide (2 ml). The reaction mixture was stirred overnight at 100° C. under heating. The reaction mixture was cooled to room temperature, added to ice water, basified with a sodium bicarbonate solution, and then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 28 mg of the titled compound as a white solid.

Aufarbeitung

  1. temperatureunder heating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v)
  7. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-67da35e630ba47e59d14e5a0b656c33a
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188114B2

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