Bis[2-(diphenylphosphino)phenyl] ether → 6-[(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)thio]-4-[(3-methoxyphenyl)amino]quinoline-3-carboxamide

HRID 230853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230853
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH:14]C(=O)OC(C)(C)C)=[O:13])=[C:5]2[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([SH:45])=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([NH2:14])=[O:13])=[C:5]3[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Komponenten

8

Edukt 4

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 11701480Benzenethiol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-HCID 23665647Potassium tert-butoxideHCID 57763225HCID 57763225, Verbindung

Produkt 1

HCID 577632316-[(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)thio]-4-[(3-methoxyphenyl)amino]quinoline-3-carboxamideAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred mixture of Intermediate 37 (0.8 g) and 4-{[tert-butyl(dimethyl)silyl]oxy} benzenethiol (0.74 g, EP465802A1), with (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.05 g), potassium tert-butoxide (0.26 g) and tris(dibenzylideneacetone) dipalladium(0) (0.08 g) in toluene (30 ml) was heated at 106° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (25 ml) and washed with a sodium carbonate solution (30 ml). The organic extracts were washed with water (30 ml) , dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate/diethyl ether (7:3) as the eluent. The appropriate fractions were concentrated in vacuo to give the title compound as a yellow foam (0.38 g).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washwashed with a sodium carbonate solution (30 ml)
  3. washThe organic extracts were washed with water (30 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel
  7. concentrationThe appropriate fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6f28e2cc1304101b966e5107ae9d6a1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566786B2

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