Pyridine → 1-[2-(5-Bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanone

HRID 712754

Reaktionsgleichung

Reaktionsgleichung von HRID 712754
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[CH:7]=1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:19](=[O:21])[CH3:20])[CH:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 44038153-Bromo-5-(pyrrolidin-2-yl)pyridine

Produkt 1

HCID 1176672401-[2-(5-Bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanoneAusbeute 132 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-5-(2-pyrrolidinyl)pyridine (200 mg, 0.881 mmol) and pyridine (0.2 mL, 1.96 mmol) in DCM (1 mL) in a 8-mL vial is added acetic anhydride (0.093 mL, 0.969 mmol) dropwise. The mixture is stirred at room temperature for 2.5 h. The mixture is concentrated. The resulting crude product is purified by normal phase chromatography using 0-4.5% MeOH in DCM as the gradient to afford 1-[2-(5-bromo-pyridin-3-yl)-pyrrolidin-1-yl]-ethanone (313 mg, 83% yield).

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. customThe resulting crude product is purified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-621fe542518d4dd4a7d446037a497fb3
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181272B2

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