Potassium Carbonate → Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

HRID 2356602

Reaktionsgleichung

Reaktionsgleichung von HRID 2356602
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[C:30]([F:36])[CH:29]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:32][C:31]2[CH:34]=[CH:35][C:28]([Cl:27])=[CH:29][C:30]=2[F:36])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27365514-Chloro-2-fluorobenzyl bromideHCID 59384254Ethyl 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylate

Produkt 1

HCID 59384237Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of ethyl 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylate (92 mg, 0.31 mmol), potassium carbonate (109 mg, 2.5 equivalents) and 4-chloro-2-fluorobenzyl bromide (78 mg, 1.1 equivalents) in acetone (˜6 ml) was heated at 50° C. for 3-4 hours until there was no more SM (starting material). Cooled down, filtered off and washed with acetone. LC/MS okay, Rt4.05. Purified by SPE, product came off with ˜20% ethyl acetate in iso-hexane. 108 mg of a white solid. Rt=4.05 [MH+] 434, 437.

Aufarbeitung

  1. temperatureCooled down
  2. filtrationfiltered off
  3. washwashed with acetone
  4. customPurified by SPE, product

Quellen und Nachweise

ORD-Eintrag
ord-1767e321d4734fb3bbc95fa506276705
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759369B2

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