Ethanol → HCID 20095020, compound

HRID 1770171Notes

Reaction equation

HRID 1770171 reaction equation
[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12](B(O)O)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl[C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=1.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.CC(C)=O.O.C1C=CC=CC=1>[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:20]3[CH:28]=[CH:27][C:23]([C:24](=[O:25])[NH2:26])=[CH:22][N:21]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 804566-ChloronicotinamideHCID 20095048HCID 20095048, compound

Product 1

HCID 20095020HCID 20095020, compoundYield 92.2%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 180AcetoneSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

5.00 g (20.3 mM) of 2-hexylindan-5-boronic acid, 2.79 g (17.8 mM) of 6-chloronicotinamide, 20 ml of ethanol, 30 ml of benzene, 27.9 ml of 2M-sodium carbonate aqueous solution and 1.19 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 2 hours under stirring. After the reaction, the reaction mixture was poured into water to obtain an insoluble matter. The insoluble matter was recovered by filtration. Separately, the filtrate was subjected to vacuum distillation to remove the organic solvent and poured into water to obtain an insoluble matter. The insoluble matter was added to the above-prepared insoluble matter. To the resultant mixture, 100 ml of acetone was added, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration and washed with acetone, followed by drying to obtain 5.30 g of 2-hexyl-5-(5-carbamoylpyridine-2-yl)indan (Yield: 92.2%).

Workup

  1. temperatureheat-refluxed for 2 hours
  2. customAfter the reaction
  3. customto obtain an insoluble matter
  4. filtrationThe insoluble matter was recovered by filtration
  5. distillationSeparately, the filtrate was subjected to vacuum distillation
  6. customto remove the organic solvent
  7. additionpoured into water
  8. customto obtain an insoluble matter
  9. additionThe insoluble matter was added to the above-prepared insoluble matter
  10. temperatureby cooling with ice
  11. customto precipitate a crystal
  12. filtrationThe crystal was recovered by filtration
  13. washwashed with acetone
  14. customby drying

Sources & evidence

ORD record
ord-abe603d5d53245598389d996423d1244
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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