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

HRID 1770181Notes

Reaction equation

HRID 1770181 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

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##

Workup

  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)

Sources & evidence

ORD record
ord-5ebd1f6055524708aa6f59f76a73ae66
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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