Diisopropylethylamine → Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinate

HRID 72436

Reaktionsgleichung

Reaktionsgleichung von HRID 72436
Cl[C:2]1[N:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1([CH:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[Cl:12][C:9]1[CH:10]=[N:11][C:2]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 2764318Methyl 2,5-Dichloronicotinate

Produkt 1

HCID 67958237Methyl 5-chloro-2-(2-phenylpyrrolidin-1-yl)nicotinateAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of Methyl 2,5-dichloronicotinate (120 mg, 0.58 mmol,) in isopropanol (10 ml), 2-phenylpyrrolidine (86 mg, 0.58 mmol, available from Matrix Scientific #018619) and N,N-Diisopropylethylamine (90 mg, 0.70 mmol) were added. The mixture was heated under reflux overnight. After cooling to room temperature, the mixture was evaporated and the residue was dissolved in ethyl acetate (10 ml), washed with water (10 ml) and brine (10 ml), dried over Na2SO4 and evaporated in vacuo. The crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 20:1 to afford the title compound (D72) (167 mg) as colorless oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe mixture was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  5. washwashed with water (10 ml) and brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customThe crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 20:1

Quellen und Nachweise

ORD-Eintrag
ord-5e3375791b904b1f97f0e2e9f6e535f8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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