Sodium hydride → 5-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

HRID 624842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624842
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.C[O:9][C:10]([C:12]1[C:17](C)=[CH:16][C:15]([Br:19])=[C:14](Cl)[N:13]=1)=[O:11]>>[Br:19][C:15]1[CH:16]=[CH:17][C:12]([C:10]([OH:11])=[O:9])=[N:13][C:14]=1[O:7][CH2:6][CH:3]1[CH2:5][CH2:4]1

Komponenten

4

Edukt 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 86674738Methyl 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester

Produkt 1

HCID 710875435-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acidAusbeute 76,7 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (4.83 g, 0.12 mol) was added into cyclopropanemethanol (CAN 2516-33-8, 30 g) at 0° C. and the mixture was stirred at 0° C. for 1 h. Then to the mixture was added methyl 5-bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (3 g, 12.75 mmol). The obtained solution was heated to 90° C. for 2 h. Then the mixture was evaporated to dryness, the residue was dissolved in 40 mL of water, and adjusted to pH=4 with hydrochloric acid (3 N), and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with water (2×30 mL) and brine (2×50 mL) then evaporated to dryness to obtain the product as a white solid (2.5 g, 76.7%); MS (EI): m/e=272.0 [MH+].

Aufarbeitung

  1. temperatureThe obtained solution was heated to 90° C. for 2 h
  2. customThen the mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in 40 mL of water
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic layer was washed with water (2×30 mL) and brine (2×50 mL)
  6. customthen evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3afc53ff6ec7461f9272a9689976909a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303012B2

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