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

HRID 8785

반응식

HRID 8785 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1e05681d149548b4b3f14d7ef43684ef
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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