Toluene → HCID 59578015, compound

HRID 2194157Notes

Reaction equation

HRID 2194157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:21][CH2:20][C:14]2([C:18](=[O:19])[NH:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].I[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>CCOC(C)=O.[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:21][CH2:20][C:14]2([C:18](=[O:19])[N:17]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:9])=[O:10]

Participants

9

Reactant 4

HCID 1140TolueneHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 23676156Sodium t-butoxideHCID 595779948-(2-Chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 59578015HCID 59578015, compoundYield 23.7%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

As an alternative, this material was prepared through a palladium-catalyzed coupling in analogy to a procedure described in literature: W. E Shakespeare, Tetrahedron Lett. 1999, 40 p 2035): A mixture of 8-(2-chloro-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.085 g), palladium(II) acetate (0.012 g), 1,1′-bis(diphenylphosphino)-ferrocene (0.021 g) was treated under an argon atmosphere at RT with 4-iodobenzotrifluoride (0.211 g in toluene, 5 ml) and sodium tert-butoxide (0.142 g). More toluene (5 ml) was added and the mixture was then heated at 120° C. for 23 h. It was then cooled to RT, diluted with AcOEt and filtered through Celite. The filtrate was washed with aqueous NH4Cl, brine, dried over Na2SO4 and concentrated onto silica gel. Flash chromatography (eluent; MeOH/CH2Cl2 0 to 5%) gave the desired compound as a light brown solid (0.029 g). 473.1 (MH+)

Workup

  1. temperatureIt was then cooled to RT
  2. filtrationfiltered through Celite
  3. washThe filtrate was washed with aqueous NH4Cl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-63d624ef571d4ee6ad3cc8f08b00a9bb
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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