Ethyl Acetate → N-benzyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide

HRID 1665004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1665004
[CH2:1]([N:8]([CH2:22][C:23]1[S:24][C:25](Br)=[CH:26][CH:27]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][S:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31].C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[CH2:1]([N:8]([CH2:22][C:23]1[S:24][C:25]([C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:38]=2)=[CH:26][CH:27]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 67439229N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide

Produkt 1

HCID 25234174N-benzyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamideAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under argon to a stirred suspension of N-benzyl-N-(5-bromo-thiophen-2-ylmethyl)-2-trifluoromethyl-benzenesulfonamide (89 mg) and (3-methylsulfonylphenyl)-boronic acid (55 mg) in dioxane (0.5 mL), water (0.3 mL) and a 2 M Na2CO3 solution (0.27 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane adduct (7 mg). The mixture was stirred for 3.5 h at 80° C. Ethyl acetate was added and the mixture was washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 7:3) to give N-benzyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (88 mg) as a light yellow oil. MS: 582.6 ([M+NH4]+)

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-9945963ed0b14e1f9dc99cd7b0f735ff
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039493B2

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