Potassium Carbonate → Ethyl 4-(acetylamino)-2''-[(phenylmethyl)oxy]-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-2-carboxylate

HRID 269577

Reaktionsgleichung

Reaktionsgleichung von HRID 269577
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=2B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22]([NH:25][C:26]1[CH:27]=[C:28]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2Br)=[CH:30][CH:31]=1)(=[O:24])[CH3:23].C(=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>[C:22]([NH:25][C:26]1[CH:27]=[C:28]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:29]([C:32]2[C:33]([C:10]3[CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:30][CH:31]=1)(=[O:24])[CH3:23]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 21863594Toluene ethanolHCID 230053392-Benzyloxy-5-trifluoromethylphenylboronic acidHCID 69312172Ethyl 4-(acetylamino)-2'-bromo-2-biphenylcarboxylate

Produkt 1

HCID 58731007Ethyl 4-(acetylamino)-2''-[(phenylmethyl)oxy]-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-2-carboxylateAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of [2-[(phenylmethyl)oxy]-5-(trifluoromethyl)phenyl]boronic acid (118 mg, 0.4 mmol), ethyl 4-(acetylamino)-2′-bromo-2-biphenylcarboxylate (121 mg, 0.33 mmol), potassium carbonate (414 mg, 3 mmol) and tetrakis(triphenylphosphine)palladium(0) (39 mg, 0.033 mmol) in 1:1 toluene/ethanol (5 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 chromatographed with ethyl acetate/iso-hexane (1:2) to yield 121 mg of the title compound as a colourless gum.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was chromatographed with ethyl acetate/iso-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-5762e637f19e499db5f736da462d0b2c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

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