Sodium Carbonate → Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

HRID 1064654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064654
CS(O[CH2:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][C:11]=2[CH:12]=1)(=O)=O.Br.[CH3:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:26][C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][C:11]=2[CH:12]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 113936782-[5-(4-cyanophenyl)-1-benzofuran-2-yl]ethyl MethanesulfonateHCID 12444175(2R)-2-methylpyrrolidine hydrobromide

Produkt 1

HCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-Ausbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A suspension of Example 1C (0.19 g, 0.55 mmol), (2R)-2-methylpyrrolidine hydrobromide (0.17 g, 1.0 mmol) and sodium carbonate (0.23 g, 2.2 mmol) in acetonitrile (0.4 mL) was heated to 50° C. with stirring for 48 hours. The reaction was cooled to ambient temperature, diluted with acetonitrile and centrifuged. The supernatant liquid was removed and the solids washed with acetonitrile. The combined liquids were concentrated under reduced pressure and the residue chromatographed by reverse phase HPLC with aqueous CF3CO2H/acetonitrile to give the titled compound (0.065 g, 34%). 1H NMR (300 MHz, CD3OD) δ7.88 (m, 1H), 7.71 (m, 4H), 7.50 (m, 2H), 6.82 (s, 1H), 3.72-3.9 (m, 2H), 3.58 (m, 1H), 3.25-3.5 (m, 4H), 2.48 (m, 1H), 2.05-2.2 (m, 2H), 1.75 (m, 1H), 1.50 (d, J=6 Hz, 3H); MS (DCI) m/z 331 (M+H)+;

Aufarbeitung

  1. customThe supernatant liquid was removed
  2. washthe solids washed with acetonitrile
  3. concentrationThe combined liquids were concentrated under reduced pressure
  4. customthe residue chromatographed by reverse phase HPLC with aqueous CF3CO2H/acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-de5b6893e9af4065930ebdeda1dafabf
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969730B2

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