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Hydrochloric Acid → 6-(3-Ethoxyphenyl)nicotinic acid

HRID 388382
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 388382
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C>[CH2:11]([O:13][C:14]1[CH:19]=[C:18]([C:2]2[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2389326-Bromonicotinic acidHCID 27739203-Ethoxybenzeneboronic acid

Produkt 1

HCID 532232596-(3-Ethoxyphenyl)nicotinic acidAusbeute 24,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel2×
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 6-bromo-3-pyridinecarboxylic acid (Sigma-Aldrich; 100 mg, 0.495 mmol) in 1,2-dimethoxyethane (9 ml) was added [3-(ethyloxy)phenyl]boronic acid (Sigma-Aldrich; 247 mg, 1.485 mmol), sodium carbonate (315 mg, 2.97 mmol) pre-dissolved in water (1 ml) and bis(triphenylphosphine)palladium(II)chloride (52.1 mg, 0.074 mmol). The mixture was heated at 140° C. for 30 mins in a microwave reactor (high absorbance). Ethyl acetate and water were added followed by aqueous HCl (5M). The aqueous layer was extracted with more ethyl acetate. The organic layers were evaporated to dryness and purified using a 5 g SAX column which was pre conditioned with MeOH. The column was washed with MeOH (2 column volumes) and then eluted with 0.5M NH3/MeOH. The eluant was evaporated to dryness under reduced pressure to give a yellow solid. Purification by MDAP gave the title compound as a white solid (29 mg);

Aufarbeitung

  1. extractionThe aqueous layer was extracted with more ethyl acetate
  2. customThe organic layers were evaporated to dryness
  3. custompurified
  4. washThe column was washed with MeOH (2 column volumes)
  5. washeluted with 0.5M NH3/MeOH
  6. customThe eluant was evaporated to dryness under reduced pressure
  7. customto give a yellow solid
  8. customPurification by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-0fa15fd94730425abcd669c6040a1d54
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08377941B2

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