Dimethyl Sulfoxide → 1-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol

HRID 338534

Reaktionsgleichung

Reaktionsgleichung von HRID 338534
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1.C(N(CC)CC)C.CS(C)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:11]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]2)=[N:4][C:3]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 532174543-Bromo-6-chloro-2-methoxypyridine

Produkt 1

HCID 866988541-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-olAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A vial was charged with 3-bromo-6-chloro-2-methoxypyridine (1.00 g, 4.5 mmol), rac-pyrrolidin-3-ol (0.59 g, 6.7 mmol), triethylamine (0.91 g, 8.9 mmol) and dimethylsulfoxide (4 mL). The mixture was heated to 150° C. for 5 hrs. The mixture was cooled to room temperature and diluted with 20 mL of water. The solution was extracted with ethyl acetate (10 mL×3). The extracts were combined, dried (sodium sulfate) and concentrated. The resulting residue was purified through flash column chromatography (petroleum ether/ethyl acetate=5:1˜2:1) to give the title compound (0.26 g, 25.3%) as light brown gum.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe solution was extracted with ethyl acetate (10 mL×3)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting residue was purified through flash column chromatography (petroleum ether/ethyl acetate=5:1˜2:1)

Quellen und Nachweise

ORD-Eintrag
ord-d9b7bf7e5fd34fa3876bbc5209f12362
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

Verknüpfte Notizen

Wird geladen…