Water → HCID 58985096, compound

HRID 1158722Notes

Reaction equation

HRID 1158722 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[O:14]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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>[O:14]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[C:4]([N:8]3[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 27571541-(3-Bromophenyl)piperazine

Product 1

HCID 58985096HCID 58985096, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixed solution of 1-(3-bromophenyl)-piperazine (100 mg, 0.415 mmol), 3-furylboronic acid (69.6 mg, 0.622 mmol), tetrakis(triphenylphosphine)palladium (57.5 mg, 0.050 mmol), 2N aqueous solution of sodium carbonate (1.66 ml, 3.32 mmol) in toluene (4.0 ml) was stirred at 95° C. for 14 hours under a nitrogen atmosphere. After cooling to room temperature, water was poured into the reaction solution, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give the titled compound 45.4 mg (47.9%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8101986c344e4750b997d69584f408c8
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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