1,3-Benzodioxol-5-amine → HCID 18549632, compound

HRID 1266186Notes

Reaction equation

HRID 1266186 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](I)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(C)(C)C.[K+].[CH2:66]1[O:75][C:74]2[CH:73]=[CH:72][C:70]([NH2:71])=[CH:69][C:68]=2[O:67]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.ClCCl>[CH2:66]1[O:75][C:74]2[CH:73]=[CH:72][C:70]([NH:71][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)=[CH:69][C:68]=2[O:67]1

Participants

9

Reactant 4

HCID 843101,3-Benzodioxol-5-amineHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 18549632HCID 18549632, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

10 mmol of 3,4,5-trimethoxyiodobenzene, 0.4 mmol of palladium acetate, 0.4 mmol of 2,2′-bis(diphenylphosphino)-1,1′-bi naphthyl and 14 mmol of potassium tert-butanolate are added to 10 mmol of 3,4-methylenedioxyaniline dissolved in toluene. After heating for 15 minutes at 100° C., the reaction mixture is brought to ambient temperature, and then dichloromethane and water are added. The organic phase is subsequently separated off and distilled under reduced pressure. The residue is purified by chromatography on silica, using dichloromethane as eluant, to yield the expected product in the form of an oil.

Workup

  1. customis brought to ambient temperature
  2. customThe organic phase is subsequently separated off
  3. distillationdistilled under reduced pressure
  4. customThe residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-a122374ed13e4c20aca43234d87c45de
Source dataset
uspto-grants-2003_04
Patent number
US06548515B1

Reaction notes

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