Sodium Carbonate → 2-(tert-Butoxycarbonylamino)-5-[(E)-2-(4-methylphenyl)ethenyl]indan

HRID 1581961Notes

Reaction equation

HRID 1581961 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](/[CH:34]=[CH:33]/[C:30]3[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=3)[CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 6019835[(E)-2-(4-Methylphenyl)ethenyl]boronic acidHCID 22719604HCID 22719604, compound

Product 1

HCID 227196342-(tert-Butoxycarbonylamino)-5-[(E)-2-(4-methylphenyl)ethenyl]indanYield 78.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

2-(tert-butoxycarbonylamino)-5-trifluoromethanesulfonyloxyindan (260 mg, 0.69 mmol), (E)-2-(4-methylphenyl)ethenylboronic acid (180 mg), toluene (7 ml), Pd(PPh3)4 (30 mg, 0.026 mmol), 2M sodium carbonate (0.99 ml), ethanol (3.0 ml), and lithium chloride (64 mg, 1.5 mmol) were heated to reflux for 5 hours. The reaction mixture was diluted with ether, washed with water, dried, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to obtain the title compound (190 mg, 0.54 mmol) having the following physical properties;

Workup

  1. temperatureto reflux for 5 hours
  2. washwashed with water
  3. customdried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6e54ecd1c70241f9bfb1049af5f3c3a3
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

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