2-(Di-tert-butylphosphino)biphenyl → (r)-4-(3-Methylpiperazin-1-yl)-n-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

HRID 1715891Notes

Reaction equation

HRID 1715891 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:17][C@@H:18]1[CH2:23][NH:22][CH2:21][CH2:20][NH: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>[CH3:17][C@H:18]1[NH:19][CH2:20][CH2:21][N:22]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:16][N:15]=[CH:14][N:13]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 27342152-(Di-tert-butylphosphino)biphenylHCID 73304342-Methylpiperazine, (R)-HCID 536276064-bromo-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 59465674(r)-4-(3-Methylpiperazin-1-yl)-n-(1,2,4-thiadiazol-5-yl)benzenesulfonamideYield 19%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Synthesized according to general procedure 8. The reaction was set up with 4-bromo-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (4.7 mmol), (R)-2-methylpiperazine (4.7 mmol), Pd2(dba)3 (0.12 mmol), 2-(di-t-butylphosphino)biphenyl (0.50 mmol), NaO-tBu (10 mmol), and toluene (12 mL). For the purification, 10% MeOH in CH2Cl2 with the addition of 1% triethylamine was used as a solvent system to obtain the desired amine as a white solid (300 mg, 19% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=340.2; tR=1.56 min.

Workup

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

Sources & evidence

ORD record
ord-b58714475eb243de9711f9e385f50dce
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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