Ethanol → 2-Octyl-5-[4-(2-octylpyrimidine-5-yl)phenyl]indan

HRID 1770170노트

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HRID 1770170 반응식
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:21]([C:29]1[N:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38](Br)=[CH:37][CH:36]=2)=[CH:31][N:30]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:38]3[CH:37]=[CH:36][C:35]([C:32]4[CH:31]=[N:30][C:29]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[N:34][CH:33]=4)=[CH:40][CH:39]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 200950552-Octyl-5-(4-bromophenyl)pyrimidineHCID 220990862-Octylindane-5-boronic acid

생성물 1

HCID 200950662-Octyl-5-[4-(2-octylpyrimidine-5-yl)phenyl]indan수율 71.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 241Benzene용매

실험 절차

0.41 g (1.50 mM) of 2-octylindan-5-boronic acid, 0.45 g (1.30 mM) of 2-octyl-5-(4-bromophenyl)pyrimidine, 2.2 ml of ethanol, 4.2 ml of benzene, 2.1 ml of 2M-sodium carbonate aqueous solution and 0.07 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 200 minutes under stirring. After the reaction, the reaction mixture was poured into ice water and subjected to extraction with ethyl acetate, followed by washing with saturated common salt aqueous solution. The organic layer was dried with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the organic layer and the resultant organic layer was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent (toluene/acetone) and ethyl acetate to obtain 0.46 g of 2-octyl-5-[4-(2-octylpyrimidine-5-yl)phenyl]indan (Yield: 71.5%). ##STR301##

후처리

  1. temperatureheat-refluxed for 200 minutes
  2. customAfter the reaction
  3. extractionsubjected to extraction with ethyl acetate
  4. washby washing with saturated common salt aqueous solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customThen, the sodium sulfate was removed from the organic layer
  7. customthe resultant organic layer was evaporated
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  10. customrecrystallized from a mixture solvent (toluene/acetone) and ethyl acetate

출처 및 근거

ORD 기록
ord-cd3fd18b659048ed9df0a73a9ea0158a
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05385692

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