1-Methylpiperazine → HCID 68707998, compound

HRID 222108Notes

Reaction equation

HRID 222108 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:20][C:11]3=[C:12]4[C:17](=[CH:18][CH:19]=[C:10]3[CH:9]=2)[CH:16]=[N:15][CH:14]=[CH:13]4)=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:46][N:47]1[CH2:52][CH2:51][N:50]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:20][C:11]4=[C:12]5[C:17](=[CH:18][CH:19]=[C:10]4[CH:9]=3)[CH:16]=[N:15][CH:14]=[CH:13]5)=[CH:4][CH:3]=2)[CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 68708248HCID 68708248, compound

Product 1

HCID 68707998HCID 68707998, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To 2-(4-bromo-phenyl)-1H-pyrrolo[2,3-f]isoquinoline XIXB (1.54 mmol), 2-(dicyclohexylphosphino)biphenyl (0.154 mmol), palladium acetate (0.154 mmol) and 1-methylpiperazine (15.46 mmol), degassed DMF (5 mL) and sodium tert-butoxide (4.62 mmol) were added. The mixture was submitted to microwaves at 150° C. for 15 min, the solvent was removed and the crude was purified by chromatography on silica gel (eluant: DCM/MeOH/30% aq NH3 92:8:1) affording the title compound (79% yield). ESI (+) MS: m/z 343 (MH+). 1H NMR: 2.24 (s, 3H), 2.45-2.50 (m, 4H), 3.20-3.26 (m, 4H), 6.96 (d, J=1.46, 1H), 7.07 (d, J=8.90, 2H), 7.58 (d, J=8.54, 1H), 7.78 (d, J=8.54, 1H), 7.85 (d, J=8.90, 2H), 8.43 (d, J=5.85, 1H), 8.50 (d, J=5.73, 1H), 9.18 (s, 1H), 12.33 (s, 1H).

Workup

  1. additionwere added
  2. customthe solvent was removed
  3. customthe crude was purified by chromatography on silica gel (eluant: DCM/MeOH/30% aq NH3 92:8:1)

Sources & evidence

ORD record
ord-7ab2347aabd54d8abbf226477cfc0ee9
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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