Potassium Carbonate → Methyl 4-(acetylamino)-2''-{[(2, 4-difluorophenyl)methyl]oxy}-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-2-carboxylate

HRID 269566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269566
[F:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1B(O)O.[C:24]([NH:27][C:28]1[CH:29]=[C:30]([C:41]([O:43][CH3:44])=[O:42])[C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2Br)=[CH:32][CH:33]=1)(=[O:26])[CH3:25].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:24]([NH:27][C:28]1[CH:29]=[C:30]([C:41]([O:43][CH3:44])=[O:42])[C:31]([C:34]2[C:35]([C:7]3[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=3[O:5][CH2:4][C:3]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:2]=3[F:1])=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:32][CH:33]=1)(=[O:26])[CH3:25]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 211129052-(2,4-Difluorobenzyloxy)-5-trifluoromethylphenylboronic acidHCID 21863594Toluene ethanolHCID 58731002Methyl 4-(acetylamino)-2'-bromo-2-biphenylcarboxylate

Produkt 1

HCID 58731000Methyl 4-(acetylamino)-2''-{[(2, 4-difluorophenyl)methyl]oxy}-5''-(trifluoromethyl)-1,1':2',1''-terphenyl-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-[(2,4-difluorobenzyl)oxy]-5-trifluoromethylbenzene boronic acid (66 mg, 0.2 mmol), methyl 4-(acetylamino)-2′-bromo-2-biphenylcarboxylate (110 mg, 0.32 mmol), potassium carbonate (138 mg, 1 mmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 5 mol %) in 1:1 toluene/ethanol (4 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 (2:3) to yield the title compound as a pale yellow gum. (90 mg).

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 (2:3)

Quellen und Nachweise

ORD-Eintrag
ord-2c3b5cb6f228406ab194bb627af8d4be
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446222B2

Notizen zur Reaktion

Wird geladen…