Ethanol → HCID 20095031, compound

HRID 1770174Notes

Reaction equation

HRID 1770174 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]1N=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=1.[CH2:29](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:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:20]3[CH:29]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][N:21]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 825442-Chloro-5-nitropyrimidineHCID 20095048HCID 20095048, compound

Product 1

HCID 20095031HCID 20095031, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

1.00 g (4.06 mM) of 2-hexylindan-5-boronic acid, 0.64 g (4.04 mM) of 2-chloro-5-nitropyrimidine, 5 ml of ethanol, 6 ml of benzene, 5.6 ml of 2M-sodium carbonate aqueous solution and 0.24 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 30 minutes under stirring. After the reaction, the reaction mixture was subjected to filtration under reduced pressure to obtain an insoluble matter. The insoluble matter was washed with ethyl acetate and recrystallized from acetone to obtain 1.02 g of 2-hexyl-5-(5-nitropyridine-2-yl)indan (Yield: 77.4%).

Workup

  1. temperatureheat-refluxed for 30 minutes
  2. customAfter the reaction
  3. filtrationthe reaction mixture was subjected to filtration under reduced pressure
  4. customto obtain an insoluble matter
  5. washThe insoluble matter was washed with ethyl acetate
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-15bc7e5dc48c4386bb776bd73771beb9
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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