Boron trifluoride etherate → N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-phenyl)-N-methyl-benzenesulfonamide

HRID 1452547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452547
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:33])[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1)(O)[C:12]([F:15])([F:14])[F:13])[CH3:2].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:33])[S:24]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:25])=[O:26])=[CH:19][CH:18]=1)[C:12]([F:13])([F:14])[F:15])[CH3:2]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 21943462N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide

Produkt 1

HCID 21943465N-(4-{1-[1-(2-Ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-phenyl)-N-methyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 32 mg (0.07 mmol) of N-(4-{1-[1-(2-ethoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide (see, Preparative Example A) in 2 mL of CH2Cl2 at 0° C. were added 1.05 mL (6.57 mmol) of triethylsilane followed by 167 μL (1.32 mmol) of boron trifluoride diethyl etherate dropwise. The mixture was warmed to room temperature and stirred for 1.75 h. After this time, the reaction mixture was cooled to 0° C., quenched by the addition of a saturated aqueous solution of sodium bicarbonate, allowed to warm to room temperature, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound.

Aufarbeitung

  1. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  2. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate
  3. temperatureto warm to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-119227033f5544bb9573f6076a4a283a
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473703B2

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