Potassium Carbonate → 2-Benzyloxy-[1,1';2',1'']terphenyl-4''-sulfonic acid (1-phenyl-methanoyl)-amide

HRID 269543

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16](B(O)O)=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:36])(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)(=O)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:37]1([C:35]([NH:34][S:31]([C:28]2[CH:29]=[CH:30][C:25]([C:16]3[C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:26][CH:27]=2)(=[O:33])=[O:32])=[O:36])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 2′-benzyloxy-biphenyl-2-boronic acid (100 mg, 0.33 mmol), 4-bromo-N-(1-phenyl-methanoyl)-benzenesulfonamide (95 mg, 0.28 mmol), potassium carbonate (309 mg, 2.24 mmol), and tetrakis(triphenylphosphine)palladium(0) (38 mg, 0.033 mmol) in 1:1 toluene/ethanol (5 ml) was stirred and heated at 90° C. under nitrogen for 16 hours. After cooling the mixture was diluted with ethyl acetate and water. The organic phase was dried and evaporated. The residue was chromatographed eluting with ethyl acetate/iso-hexane (1:4-1:1) to give the title compound as a colourless solid. (40 mg 23%).

Aufarbeitung

temperatureAfter cooling the mixture
customThe organic phase was dried
customevaporated
customThe residue was chromatographed
washeluting with ethyl acetate/iso-hexane (1:4-1:1)

Quellen und Nachweise

ORD-Eintrag: ord-f223f0c3235c49968b831589534a2cf9
Quelldatensatz: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07446222B2

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