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

HRID 1770181
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HRID 1770181 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].O([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:37][N:36]=2)=[CH:31][C:30]=1[F:51])S(C(F)(F)F)(=O)=O.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.C1(C)C=CC=CC=1.O>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[N:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:37][N:36]=4)=[CH:31][C:30]=3[F:51])[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 200950522-Fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflateHCID 220990862-Octylindane-5-boronic acid

생성물 1

HCID 200950462-Octyl-5-[2-fluoro-4-(5-decylpyrimidine-2-yl)phenyl]indan수율 86.3%

시약·촉매·용매 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 962Water용매
HCID 1140Toluene용매2회

실험 절차

0.53 g (1.93 mM of 2-octylindan-5-boronic acid, 0.80 g (1.73 mM) of 2-fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflate, 1.5 ml of ethanol, 2.7 ml of toluene, 2.7 ml of 2M-sodium carbonate aqueous solution and 0.09 g of tetrakis (triphenylphosphine) palladium (0) were mixed and heat-refluxed for 130 minutes under stirring. After the reaction, the reaction mixture, water and toluene were added to followed by filtration under reduced pressure. The toluene layer was washed with a common salt aqueous solution 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) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.81 g of 2-octyl-5-[2-fluoro-4-(5-decylpyrimidine-2-yl)phenyl]indan (Yield: 86.3%). ##STR314##

후처리

  1. temperatureheat-refluxed for 130 minutes
  2. customAfter the reaction
  3. filtrationto followed by filtration under reduced pressure
  4. washThe toluene layer was washed with a common salt aqueous solution
  5. dry with materialby drying with anhydrous sodium sulfate
  6. customThen, the sodium sulfate was removed from the mixture
  7. customthe resultant mixture was evaporated
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  10. customrecrystallized from a mixture solvent (toluene/methanol)

출처 및 근거

ORD 기록
ord-5ebd1f6055524708aa6f59f76a73ae66
출처 데이터셋
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05385692

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