Sodium Carbonate → (4-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenoxy)acetic acid ethyl ester

HRID 1766753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766753
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:19]([O:21][C:22](=[O:40])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28](C2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=1)[CH3:20].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CN(C=O)C.O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:19]([O:21][C:22](=[O:40])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:7]=[N:6][C:5]([NH2:8])=[C:4]([O:9][CH2:10][C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[CH:3]=2)=[CH:27][CH:26]=1)[CH3:20]

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 211114873-(2,6-Dichlorobenzyloxy)-5-bromopyridin-2-amineHCID 66701800[4-(4,4,5,5-Tetramethyl-(1,3]dioxolan-2-yl)-phenoxy]-acetic acid ethyl ester

Produkt 1

HCID 66701842(4-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenoxy)acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3-(2,6-dichloro-benzyloxy)-pyridin-2-ylamine (Example I(a)) (2.2 g, 6.3 mmol), [4-(4,4,5,5-tetramethyl-(1,3]dioxolan-2-yl)-phenoxy]-acetic acid ethyl ester (2.9 g, 1.5 eq.), bis(triphenylphosphine)palladium(II) chloride (136 mg) and sodium carbonate (1.93 g, 3.0 eq.) in ethylene glycol dimethyl ether (30 mL), DMF (5 mL) and water (8 mL) was heated to 90–100° C. under nitrogen for 7 hr. The reaction was cooled to rt and diluted with ethyl acetate. The mixture was washed with water, brine, dried and purified on silica column to afford (4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenoxy)acetic acid ethyl ester. This ester was treated with sodium carbonate and water at rt overnight. The reaction was diluted with ethyl acetate. The mixture was washed with water, brine, dried and purified on silica column to afford 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenoxy}-acetic acid.

Aufarbeitung

  1. temperaturewas heated to 90–100° C. under nitrogen for 7 hr
  2. washThe mixture was washed with water, brine
  3. customdried
  4. custompurified on silica column

Quellen und Nachweise

ORD-Eintrag
ord-2d1f0e96a5d047ad94475d9c2f9cfbf9
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230098B2

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