Cesium carbonate → 1-[5-(3-Difluoromethoxy-benzenesulfonyl)-2-methyl-phenyl]-4-(toluene-4-sulfonyl)-piperazine

HRID 657489Notes

Reaction equation

HRID 657489 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.[F:25][CH:26]([F:37])[O:27][C:28]1[CH:29]=[C:30]([S:34]([O-:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:37][CH:26]([F:25])[O:27][C:28]1[CH:29]=[C:30]([S:34]([C:2]2[CH:3]=[CH:4][C:5]([CH3:24])=[C:6]([N:8]3[CH2:13][CH2:12][N:11]([S:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)(=[O:16])=[O:15])[CH2:10][CH2:9]3)[CH:7]=2)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 58258782Sodium 3-(difluoromethoxy)benzenesulfinateHCID 595639611-(5-Iodo-2-methyl-phenyl)-4-(toluene-4-sulfonyl)-piperazine

Product 1

HCID 595639691-[5-(3-Difluoromethoxy-benzenesulfonyl)-2-methyl-phenyl]-4-(toluene-4-sulfonyl)-piperazineYield 63.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

0.521 g of 1-(5-Iodo-2-methyl-phenyl)-4-(toluene-4-sulfonyl)-piperazine (1.14 mmol), 0.315 g of sodium 3-(difluoromethoxy)benzenesulfinate (1.37 mmol), 0.558 g of cesium carbonate (1.713 mmol), 0.026 g of Pd(dba)3 (0.029 mmol), 0.033 g of Xantphos (0.059 mmol) and 0.381 g of tetrabutylammonium chloride (1.37 mmol) were stirred for 8 h in 10 mL of toluene. The reaction mixture was filtered and the solvent evaporated. The crude product was purified via silica gel chromatography with toluene/methanol 20:1 (2.5% triethylamine), fractions containing the product combined and the solvents evaporated to yield 0.386 g of product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated
  3. customThe crude product was purified via silica gel chromatography with toluene/methanol 20:1 (2.5% triethylamine), fractions
  4. additioncontaining the product
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-a37392640123468da0ac0ea2f5a212ae
Source dataset
uspto-grants-2011_12
Patent number
US08076326B2

Reaction notes

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