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

HRID 1770170Notes

Reaction equation

HRID 1770170 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].[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-cd3fd18b659048ed9df0a73a9ea0158a
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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