Potassium Carbonate → 5''-Amino-2-benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

HRID 269527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269527
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]([C:23]1[CH:24]=[C:25]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2Br)[CH:26]=[C:27]([NH2:29])[CH:28]=1)=[O:22].[C:37](=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:19]([O:20][C:21]([C:23]1[CH:24]=[C:25]([C:30]2[C:35]([C:10]3[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[C:27]([NH2:29])[CH:28]=1)=[O:22])[CH3:37]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acidHCID 21863594Toluene ethanolHCID 693107195-Amino-2'-bromobiphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 587310045''-Amino-2-benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-benzyloxy-5-chloro-phenyl-boronic acid (197 mg, 0.75 mmol), 5-amino-2′-bromo-biphenyl-3-carboxylic acid methyl ester (216 mg, 0.71 mmol), potassium carbonate (828 mg, 6 mmol) and tetrakis(triphenylphosphine)palladium(0) (79 mg, 0.068 mmol) in 1:1 toluene/ethanol (8 ml) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was purified using Biotage with ethyl acetate/iso-hexane (1:4) to yield the title compound as a pale yellow gum. (288 mg, 89%).

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-3c4a7f916eea492a974ab77253e66094
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

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