Binap, (A+-)- → HCID 52942144, 화합물

HRID 17545노트

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HRID 17545 반응식
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]

참가 물질

8

반응물 4

HCID 634876Binap, (A+-)-HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 23676156Sodium t-butoxideHCID 68586325HCID 68586325, 화합물

생성물 1

HCID 52942144HCID 52942144, 화합물수율 33%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5960e71201fb4f85bbd7b014b7ff78e0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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