Piperazine → 4-(piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

HRID 2043107Notes

Reaction equation

HRID 2043107 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.O(C(C)(C)C)[Na]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[N:18]1([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 4837PiperazineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 594657044-bromo-N-(pyrimidin-4-yl)benzenesulfonamideHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 594656354-(piperazin-1-yl)-N-(pyrimidin-4-yl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Synthesized according to general procedure 4. The reaction was set up with 1.6 mmol 4-bromo-N-(pyrimidin-4-yl)benzenesulfonamide, 16.0 mmol piperazine, 0.12 mmol Pd2(dba)3, 0.15 mmol of 2-(di-t-butylphosphino)biphenyl, 10 mmol of NaO-tBu and 12 ml, toluene. For the purification, 10% MeOH in CH2Cl2 without the addition of triethylamine was used as a solvent system. Yield: 430 mg (84%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=320.2; tR=0.42 min.

Workup

  1. customSynthesized
  2. customFor the purification, 10% MeOH in CH2Cl2
  3. additionwithout the addition of triethylamine

Sources & evidence

ORD record
ord-4efbfa3b96de4d949c9059545e96d1e9
Source dataset
uspto-grants-2013_11
Patent number
US08586589B2

Reaction notes

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