Potassium Carbonate → HCID 59401866, Verbindung

HRID 415938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415938
Cl.[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1.F[C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH:8]1[CH2:12][CH2:11][N:10]([C:14]2[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=2)[CH2:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 666245402-Methyl-[1,3']bipyrrolidinyl hydrochloride2×

Produkt 1

HCID 59401866HCID 59401866, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

2-Methyl-[1,3′]bipyrrolidinyl hydrochloride (Intermediate (ii) obtained above, 5.3 g, 21.6 mmol, 1.12 equiv.) was dissolved in anhydrous DMSO (30 mL). To this solution was added 5-fluoro-2-nitrotoluene (3.00 g, 18.78 mmol, 1 equiv.), followed by powdered potassium carbonate (8.9 g, 65 mmol). The suspension was heated on an oil bath to 85° C. for 4 h when the starting material was consumed as determined by TLC (5% MeOH in DCM) and LC/MS. To the suspension were added 20 mL of water and 50 mL of DCM. The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with 5% MeOH in DCM to get the title compound as a yellow solid after drying, 5.47 g (100%). MS: 290 (M+H+).

Aufarbeitung

  1. customwas consumed
  2. additionTo the suspension were added 20 mL of water and 50 mL of DCM
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with DCM (20 mL×2)
  5. washThe combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2)
  6. dry with materialdried (anhydrous potassium carbonate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on a silica gel column
  10. washeluted with 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-b67c7f72674a4492b773312e6bb31774
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088808B2

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