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

HRID 425931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425931
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

Reaktionsbedingungen

Temperatur
95 °C

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. temperatureThe reaction was cooled to rt
  2. washThe mixture was washed with water, brine
  3. customdried
  4. custompurified on silica column

Quellen und Nachweise

ORD-Eintrag
ord-28d1f0ddea9d47568046e530eb6aadd6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106197B2

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