Thiophenol → HCID 57624598, compound

HRID 1641541Notes

Reaction equation

HRID 1641541 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:38][C:39](=[O:41])[CH3:40])([CH2:33][O:34][C:35](=[O:37])[CH3:36])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[C:20](OS(C(F)(F)F)(=O)=O)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[C:42]1([SH:48])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C>O1CCOCC1.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.C(Cl)(Cl)Cl.[Pd].[Pd].O>[C:35]([O:34][CH2:33][C:6]([NH:38][C:39](=[O:41])[CH3:40])([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]3[C:19](=[C:20]([S:48][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 57624605HCID 57624605, compound

Product 1

HCID 57624598HCID 57624598, compound

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

The compound (200 mg) of Example (1-3) was dissolved in 1,4-dioxane (700 μL), and benzenethiol (40 μL), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (9 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (10 mg) and diisopropylethylamine (120 μL) were added. The mixture was stirred at 120° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was crudely purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give a mixture (170 mg) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crudely purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3c2994b645f54c728ae851197d50fd0a
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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