Sodium Carbonate → ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

HRID 508095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508095
[F:1][C:2]1[CH:7]=[C:6]([N:8]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[CH:9]2[C:17]3[C:12](=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].[Si:45]([O:52][C:53]1[CH:58]=[C:57]([CH3:59])[C:56](B(O)O)=[C:55]([CH3:63])[CH:54]=1)([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C.C1(C)C=CC=CC=1.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>[Si:45]([O:52][C:53]1[CH:58]=[C:57]([CH3:59])[C:56]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[CH2:11][CH2:10][CH:9]3[N:8]([S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-:37])=[O:36])(=[O:28])=[O:27])[C:6]2[CH:5]=[CH:4][C:3]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:2]([F:1])[CH:7]=2)=[C:55]([CH3:63])[CH:54]=1)([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 23157502HCID 23157502, VerbindungHCID 598383324-[(Tert-butyldimethylsilyl)oxy]-2,6-dimethylphenylboronic acid

Produkt 1

HCID 68720751ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1H-inden-1-yl)amino]phenyl}propanoate (3.14 g, 4.76 mmol), (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)boronic acid (2.0 g, 7.14 mmol) and sodium carbonate (1.51 g, 14.3 mmol) were dissolved in a mixture of water (10 mL), ethanol (10 mL) and toluene (30 mL), and the air was substituted with argon gas. Tetrakis(triphenylphosphine)palladium(0) (0.275 g, 0.24 mmol) was added. The reaction mixture was stirred under an argon atmosphere at 120° C. for 16 hr. After cooling, the reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3%-60% ethyl acetate/hexane) to give ethyl 3-(4-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate as a yellow oil. The obtained oil was dissolved in tetrahydrofuran (30 mL), tetrabutylammonium fluoride (1 M THF solution, 2.43 mL, 2.43 mmol) was added under stirring at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-60% ethyl acetate/hexane) to give the title compound (1.46 g, yield 78%, 2 steps) as a yellow oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (3%-60% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d24875c9c7cf49108b3d3f90b03fdcfe
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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