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R-(+)-1,1'-联萘-2,2'-双二苯膦 → HCID 52942144,化合物

HRID 17545
笔记
打印预览

反应方程式

HRID 17545 反应方程式
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[C:53]2[CH:54]=[C:55]([C:57]([CH3:60])([CH3:59])[CH3:58])[O:56][C:52]=2[C:51]([C:61]#[N:62])=[CH:50][C:49]=1[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.[CH3:69][N:70]([CH3:76])[C@H:71]1[CH2:75][CH2:74][NH:73][CH2:72]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:57]([C:55]1[O:56][C:52]2[C:51]([C:61]#[N:62])=[CH:50][C:49]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[C:48]([N:73]3[CH2:74][CH2:75][C@H:71]([N:70]([CH3:76])[CH3:69])[CH2:72]3)[C:53]=2[CH:54]=1)([CH3:60])([CH3:59])[CH3:58]
参与物实验过程后处理来源与证据反应笔记

参与物

8

反应物 4

HCID 634876R-(+)-1,1'-联萘-2,2'-双二苯膦HCID 7019156(3S)-(-)-3-(二甲氨基)吡咯烷HCID 23676156叔丁醇钠HCID 68586325HCID 68586325,化合物

产物 1

HCID 52942144HCID 52942144,化合物收率 33%

试剂、催化剂与溶剂 3

HCID 167845乙酸钯(Ⅱ)
催化剂
HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂
HCID 1140甲苯溶剂2 次

实验过程

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (65.9 mg, 106 μmol) was dissolved under heat in toluene (1.5 ml), then cooled to room temperature, and palladium(II) acetate (15.8 mg, 70.6 μmol) was added, followed by stirring for 1 minute. 4-Bromo-2-tert-butyl-7-cyano-5-phenyl-1-benzofuran (I-258) (500 mg, 1.41 mmol), (3S)-3-(dimethylamino)pyrrolidine (215 μl, 1.69 mmol), sodium tert-butoxide (190 mg, 1.98 mmol) and toluene (1.5 ml) were successively put into it, followed by stirring at 80° C. for 14 hours. Water (30 ml) was added to the reaction liquid, the product was extracted with chloroform (50 ml×3). The organic layer was washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified twice by silica gel column chromatography (chloroform:methanol=200:1) to obtain the entitled compound (180 mg, 33%) as a yellow solid.

后处理

  1. stirringby stirring at 80° C. for 14 hours
  2. extractionthe product was extracted with chloroform (50 ml×3)
  3. washThe organic layer was washed with saturated brine (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified twice by silica gel column chromatography (chloroform:methanol=200:1)

来源与证据

ORD记录
ord-5960e71201fb4f85bbd7b014b7ff78e0
来源数据集
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
专利号
US07737166B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记