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

HRID 1770167노트

반응식

HRID 1770167 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]([O:31][C:32]1[CH:33]=[N:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=2)=[N:36][CH:37]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].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:41]3[CH:40]=[CH:39][C:38]([C:35]4[N:36]=[CH:37][C:32]([O:31][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:33][N:34]=4)=[CH:43][CH:42]=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 114747935-Decyloxy-2-(4-bromophenyl)pyrimidineHCID 220990862-Octylindane-5-boronic acid

생성물 1

HCID 200950392-Octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indan수율 82.1%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 241Benzene용매

실험 절차

0.30 g (1.09 mM) of 2-octylindan-5-boronic acid, 0.37 g (0.95 mM) of 5-decyloxy-2-(4-bromophenyl)pyrimidine, 1.8 ml of ethanol, 2.5 ml of benzene, 1.5 ml of 2M-sodium carbonate aqueous solution and 0.05 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 4 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and dissolved in toluene, followed by drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized two times from a mixture solvent (toluene/acetone) to obtain 0.42 g of 2-octyl-5-[4-(5-decyloxypyrimidine-2-yl)phenyl]indan (Yield: 82.1%). ##STR279##

후처리

  1. temperatureheat-refluxed for 4 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. dissolutiondissolved in toluene
  6. dry with materialby drying with anhydrous sodium sulfate
  7. customThen, the sodium sulfate was removed from the mixture
  8. customthe resultant mixture was evaporated
  9. customto obtain a residue
  10. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  11. customrecrystallized two times from a mixture solvent (toluene/acetone)

출처 및 근거

ORD 기록
ord-f200ceb44f0e42098f2d4ce26f9c3aeb
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05385692

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