Cesium carbonate → Ethyl {[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxy}acetate

HRID 8785

反応式

HRID 8785 の反応式
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)CO.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[C:10]([C:2]#[N:1])[C:5]([O:4][CH2:3][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:6][C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 12184Ethyl GlycolateHCID 10479445Ethyl 3-amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridine-2-carboxylate

生成物 1

HCID 86602009Ethyl {[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxy}acetate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A solution of 1.55 g (3.93 mmol) of the product from Step A in toluene (20 mL) was treated with ethyl glycolate (0.41 mL; 4.33 mmol) and cesium carbonate (2.54 g; 7.8 mmol). The reaction mixture was heated in a sealed pressure tube at 80° C. and stirred for 6 h. The reaction mixture was cooled to room temperature and 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: 460.9 (M+1), 462.9 (M+3); Rt=4.50 min.

後処理

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

出典と根拠

ORDレコード
ord-1e05681d149548b4b3f14d7ef43684ef
出典データセット
uspto-grants-2006_08
特許番号
US07091216B2

関連ノート

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