Sodium Carbonate → HCID 19921681, Verbindung

HRID 1647793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647793
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1I.[CH3:14][C:15]([Si:18]([CH3:30])([CH3:29])[O:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:15]([Si:18]([CH3:29])([CH3:30])[O:19][CH2:20][CH2:21][CH2:22][C:23]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:24]=1[Si:25]([CH3:26])([CH3:27])[CH3:28])([CH3:14])[CH3:16]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 459320Ethyl 4-amino-3-iodobenzoateHCID 10923628HCID 10923628, Verbindung

Produkt 1

HCID 19921681HCID 19921681, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-amino-3-iodobenzoate {Hirschfeld et al. J. Med Chem. 1992, 35, 2231-2238.}(7.80 g, 26.8 mmol), [5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentynyl]trimethylsilane (9.41 g, 34.8 mmol), tetra-n-butylammonium chloride (7.44 g, 26.8 mmol), sodium carbonate (14.20 g, 0.134 mol), triphenylphosphine (0.35 g, 1.3 mmol), and palladium (II) acetate (0.30 g, 1.3 mmol) in 200 mL of DMF, was heated at 98° C. under N2 for 2 h. The solution was cooled, and the bulk of the DMF was removed in vacuo. The mixture was diluted with ethyl acetate, and the organic solution was washed with aqueous NaHCO3, dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (10:1 hexanes-EtOAc) of the concentrate yielded the title compound (7.49 g, 65%) as a crystalline solid. Recrystallization from hexanes provided an analytical sample as a white crystalline solid: mp 115- 116° C. Anal. Calcd for C23H39N1O3Si2 : C 63.69; H, 9.06; N, 3.23. Found: C, 63.54; H, 9.11; N, 3.17.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customthe bulk of the DMF was removed in vacuo
  3. additionThe mixture was diluted with ethyl acetate
  4. washthe organic solution was washed with aqueous NaHCO3
  5. dry with materialdried (brine, MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8942478b94324e07b82c413ce4f54ceb
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434154

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