Sodium ethoxide → 1-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

HRID 8783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8783
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[N:10][C:11]([O:16][CH2:17][C:18](=[O:20])[CH3:19])=[C:12]([CH:15]=2)[C:13]#[N:14])=[CH:4][CH:3]=1.[O-]CC.[Na+]>C(O)C>[NH2:14][C:13]1[C:12]2[C:11](=[N:10][C:9]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:15]=2)[O:16][C:17]=1[C:18](=[O:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 219849455-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2-oxopropoxy)-nicotinonitrile

Produkt 1

HCID 104105121-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the product from Step A (0.126 g; 0.292 mmol) in ethanol (4 mL) was treated with sodium ethoxide (0.040 g; 0.584 mmol) and stirred at reflux for 1 hour. The reaction was allowed to cool to room temperature and quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 430.9 (M+1), 432.9 (M+3); Rt=4.04 min.

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. customquenched with saturated NaHCO3 solution
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate-hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7e87674c3aba466295873e89f7a3ec9d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

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