Sodium Carbonate → HCID 68918264, Verbindung

HRID 2064519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064519
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]#[C:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1.[F:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[C:32](I)[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd-2](Cl)C1C(Cl)=CC=CN=1)(C)C>[CH3:28][N:2]([CH3:1])[C:3]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:8][CH2:7][C:6]([CH2:10][CH2:11][CH2:12][C:13]2[C:35]3[C:33](=[CH:32][CH:31]=[C:30]([F:29])[CH:36]=3)[NH:34][C:14]=2[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])([OH:9])[CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27782834-Fluoro-2-iodoanilineHCID 1317299894-Dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol

Produkt 1

HCID 68918264HCID 68918264, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178439027HCID 178439027, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-dimethylamino-4-phenyl-1-(5-triethylsilanyl-pent-4-inyl)cyclohexanol (525 mg, 1.31 mmol), 4-fluoro-2-iodoaniline (374 mg, 1.58 mmol), [1,3-bis-(2,6-diisopropyl-phenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)-chloride (PEPPSI, 178 mg, 0.26 mmol) and sodium carbonate (694 mg, 6.6 mmol) was evacuated for 30 min (oil pump). It was then flushed with argon and absolute N,N-dimethylformamide (5 mL, previously flushed for 1 h with argon) was added by syringe via a Schlenk tube. The mixture was stirred for 18 h at 100° C. and changed colour to dark brown during this. The reaction mixture was then concentrated to low volume in a vacuum, the residue taken up several times in toluol (3×10 mL) and concentrated to low volume again in each case, distributed between water and ethyl acetate (20 mL each) and the phases separated again. The aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organic phases were washed with 1 M sodium thiosulphate solution (30 mL) and saturated sodium chloride solution (50 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (1.10 g) was purified by means of flash chromatography (50 g, 20×3.0 cm) with chloroform/methanol (97:3).

Aufarbeitung

  1. customwas evacuated for 30 min (oil pump)
  2. customIt was then flushed with argon and absolute N,N-dimethylformamide (5 mL
  3. custompreviously flushed for 1 h with argon)
  4. additionwas added by syringe via a Schlenk tube
  5. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  6. concentrationconcentrated to low volume again in each case
  7. customthe phases separated again
  8. extractionThe aqueous phase was extracted with ethyl acetate (2×30 mL)
  9. washthe combined organic phases were washed with 1 M sodium thiosulphate solution (30 mL) and saturated sodium chloride solution (50 mL)
  10. dry with materialdried with sodium sulphate
  11. concentrationconcentrated to low volume in a vacuum
  12. customThe raw product (1.10 g) was purified by means of flash chromatography (50 g, 20×3.0 cm) with chloroform/methanol (97:3)

Quellen und Nachweise

ORD-Eintrag
ord-ddc704ee1b30476c91b61b0737326a4d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288430B2

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