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

HRID 8782

반응식

HRID 8782 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

4

반응물 3

HCID 107572-ChloroacetophenoneHCID 10796Cesium carbonateHCID 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c15f147adfaa4abe825a35be35b3fb8b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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