Cesium carbonate → 7-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

HRID 14474

반응식

HRID 14474 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:27]([CH3:29])[CH3:28])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:82](=[NH:95])([C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:82](=[N:95][C:13]1[CH:12]=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:9]([CH:27]([CH3:29])[CH3:28])[O:10]2)=[CH:15][CH:14]=1)([C:89]1[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=1)[C:83]1[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 86625612Trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester

생성물 1

HCID 866256137-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A mixture of trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester (6.96 g, 15.6 mmol), palladium acetate (0.35 g, 1.56 mmol), cesium carbonate (12.7 g, 38.9 mmol) and racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 0.97 g, 1.56 mmol) in anhydrous tetrahydrofuran (230 ml) under an atmosphere of nitrogen is treated with benzophenone imine (3.66 g, 20.2 mmol) and allowed to stir at 80° C. for 22 hours. After allowing the resultant mixture to stir at room temperature for an additional 24 hours, it is diluted with water (300 ml) and extracted with ethyl acetate (3×300 ml). The organic extracts are combined, washed with brine, dried (MgSO4), filtered, concentrated in vacuo and purified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane) to afford the desired compound as a dark yellow solid.

후처리

  1. stirringto stir at room temperature for an additional 24 hours
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane)

출처 및 근거

ORD 기록
ord-0479cbb4c10b496d83215aa7d8ce704d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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