2-Chloroacetophenone → (3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)(phenyl)methanone

HRID 8782

Reaktionsgleichung

Reaktionsgleichung von HRID 8782
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([C:16]#[N:17])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>>[NH2:17][C:16]1[C:12]2[C:13](=[N:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:10]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH:11]=2)[O:15][C:32]=1[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]

Komponenten

4

Edukt 3

HCID 107572-ChloroacetophenoneHCID 10796Cesium carbonateHCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 9935463(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)(phenyl)methanone

Versuchsvorschrift

A solution of the product from Step B (0.300 g; 0.8 mmol) in DMP (8 mL) was treated with cesium carbonate (0.521 g; 1.6 mmol), 2-chloroacetophenone (0.124 g; 0.8 mmol), and stirred at room temperature for 16 hours. 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) afforded the title compound. HPLC/MS: 492.9 (M+1), 494.9 (M+3); Rt=4.58 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c15f147adfaa4abe825a35be35b3fb8b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091216B2

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