Triphenylarsine → HCID 59853753, compound

HRID 2374278Notes

Reaction equation

HRID 2374278 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].[CH2:30]([Sn](CCCC)(CCCC)C(C)=C)[CH2:31][CH2:32]C.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.[Cu](I)I>[C:31]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:32])=[CH2:30]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 59853753HCID 59853753, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone (Example 9; 100 mg, 0.186 mmol), Tributyl-isopropenyl-stannane (CAS: 100073-15-2; 74 mg, 0.223 mmol), Tris(dibenzylideneacetone)dipalladium chloroform complex (15.4 mg, 0.0149 mmol), Triphenylarsine (27 mg, 0.0856 mmol), Copper iodide (3.2 mg, 0.0167 mmol) in N,N-Dimethylformamide (1 ml) was heated at 90° C. for 75 minutes. The mixture was cooled to room temperature and DMF was evaporated under high vacuum. The residue was dissolved in Ethyl acetate and 4mL of a 30% Potassium fluoride solution were added. The mixture was stirred for 30 minutes. Then the aqueous phase was separated and extracted 2 times with Ethyl acetate. The organic phases were combined, washed with water, dried with Na2SO4 ,filtered and evaporated to dryness. The so obtained residue was chromatographed over SiO2 (Heptane/EtOAc 0% to 30% over 15 minutes) to provide the title compound (59 mg, 70% as a yellow solid).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customDMF was evaporated under high vacuum
  3. dissolutionThe residue was dissolved in Ethyl acetate
  4. addition4mL of a 30% Potassium fluoride solution were added
  5. customThen the aqueous phase was separated
  6. extractionextracted 2 times with Ethyl acetate
  7. washwashed with water
  8. dry with materialdried with Na2SO4
  9. customevaporated to dryness
  10. customThe so obtained residue
  11. customwas chromatographed over SiO2 (Heptane/EtOAc 0% to 30% over 15 minutes)

Sources & evidence

ORD record
ord-f4a430414fc64c5c8bc40073b7b3f930
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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