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

반응식

[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]

참가 물질

반응물 3

HCID 107572-Chloroacetophenone

HCID 10796Cesium carbonate

HCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

생성물 1

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

실험 절차

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.