3-Bromo-5-methoxypyridine → 5-Bromo-2-ethoxy-3-methoxypyridine

HRID 39357

Reaktionsgleichung

Reaktionsgleichung von HRID 39357
[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5](Cl)=[N:6][CH:7]=1.BrC1C=N[CH:15]=[C:16]([O:18]C)C=1.[O-]CC.[Na+].C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5]([O:18][CH2:16][CH3:15])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8171633-Bromo-5-methoxypyridineHCID 167481085-Bromo-2-chloro-3-methoxypyridineHCID 23706232Ethanol sodium ethoxide

Produkt 1

HCID 666174235-Bromo-2-ethoxy-3-methoxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

As shown in step 5-i of Scheme 5, 5-bromo-2-chloro-3-methoxypyridine (1.0 g, 4.5 mmol, prepared in the same manner as Compound 1003 in Example 2 starting with 3-bromo-5-methoxypyridine) was treated with a sodium ethoxide/ethanol solution (5.05 mL, 21% w/v, 13.5 mmol) and the reaction mixture microwave irradiated at 100° C. for 20 minutes. Water was added and the ethanol evaporated under reduced pressure. The resulting aqueous solution was extracted with DCM and ether, followed by drying the combined extracts over MgSO4. After filtration, removal of the volatiles under reduced pressure provided 5-bromo-2-ethoxy-3-methoxypyridine (Compound 1016), 0.72 g, 69% yield): ESMS (M+H) 232.32/234.23. As shown in step 5-ii of Scheme 5, Compound 1017 (ESMS (M+H) 218.32/220.23) was prepared in the same manner as Compound 1016, using sodium methoxide in methanol instead of sodium ethoxide in ethanol.

Aufarbeitung

  1. customthe reaction mixture microwave irradiated at 100° C. for 20 minutes
  2. customthe ethanol evaporated under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with DCM and ether
  4. dry with materialby drying the combined extracts over MgSO4
  5. filtrationAfter filtration, removal of the volatiles under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-86dc72dd18ba4196a544d017b0c63b17
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524906B2

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