Sodium Carbonate → 2-(tert-Butoxycarbonylamino)-5-[(E)-2-(4-methylphenyl)ethenyl]indan

HRID 1581961노트

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HRID 1581961 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](/[CH:34]=[CH:33]/[C:30]3[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=3)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 6019835[(E)-2-(4-Methylphenyl)ethenyl]boronic acidHCID 22719604HCID 22719604, 화합물

생성물 1

HCID 227196342-(tert-Butoxycarbonylamino)-5-[(E)-2-(4-methylphenyl)ethenyl]indan수율 78.3%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

2-(tert-butoxycarbonylamino)-5-trifluoromethanesulfonyloxyindan (260 mg, 0.69 mmol), (E)-2-(4-methylphenyl)ethenylboronic acid (180 mg), toluene (7 ml), Pd(PPh3)4 (30 mg, 0.026 mmol), 2M sodium carbonate (0.99 ml), ethanol (3.0 ml), and lithium chloride (64 mg, 1.5 mmol) were heated to reflux for 5 hours. The reaction mixture was diluted with ether, washed with water, dried, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (190 mg, 0.54 mmol) having the following physical properties;

후처리

  1. temperatureto reflux for 5 hours
  2. washwashed with water
  3. customdried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-6e54ecd1c70241f9bfb1049af5f3c3a3
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734180B1

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