2-(Di-tert-butylphosphino)biphenyl → HCID 23155763, compound

HRID 1714801Notes

Reaction equation

HRID 1714801 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21](Cl)[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[CH3:52][NH:53][CH3:54].O1CCCC1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:53]([CH3:54])[CH3:52])[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 22320367Dimethylamine tetrahydrofuranHCID 23155694HCID 23155694, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 23155763HCID 23155763, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

After dissolving 1.01 g of 1-(4-benzylpiperazin-1-yl)-7-chloroisoquinoline as synthesized in above Step 1 in 30 ml of tetrahydrofuran, 20 mg of palladium acetate, 48 mg of 2-(di-tert-butylphosphino)biphenyl, 450 mg of sodium-tert-butoxide and 5 ml of 2.0 M dimethylamine-tetrahydrofuran solution were added to the solution and sealed in a tube. This mixture was stirred at 80° C. for 16 hours. Removing the insoluble matter by filtration, the solvent was distilled off under reduced pressure and the residue was purified on silica gel column chromatography (methanol:chloroform=1:19) to provide 261 mg (25%) of 1-(4-benzylpiperazin-1-yl)-7-dimethylaminoisoquinoline.

Workup

  1. customsealed in a tube
  2. customRemoving the insoluble matter
  3. filtrationby filtration
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (methanol:chloroform=1:19)

Sources & evidence

ORD record
ord-f0bcf781f46f4b0ea4541733c3dda23a
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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