tert-Butyl acetate → tert-Butyl [1-(phenylsulfonyl)-1H-indol-4-yl]acetate

HRID 551038

Reaktionsgleichung

Reaktionsgleichung von HRID 551038
F[B-](F)(F)F.C(C1C=CC=C(C(C)C)C=1[N+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[C:46]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:47]=1[CH:48]=[CH:49][N:50]2[S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56].[C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])(=[O:66])[CH3:65]>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.[Pd].[Pd].C1(C)C=CC=CC=1>[C:58]1([S:55]([N:50]2[C:51]3[C:47](=[C:46]([CH2:65][C:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH:54]=[CH:53][CH:52]=3)[CH:48]=[CH:49]2)(=[O:57])=[O:56])[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Komponenten

7

Edukt 4

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 113750061,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborateHCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indole

Produkt 1

HCID 57426198tert-Butyl [1-(phenylsulfonyl)-1H-indol-4-yl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate (94 mg, 0.196 mmol), tris(dibenzylideneacetone)dipalladium (180 mg, 0.196 mmol), and lithium bis(trimethylsilyl)amide (1.37 M in t-BuOMe, 11.0 mL, 15.1 mmol) were added 4-bromo-1-(phenylsulfonyl)-1H-indole from Step A (2.20 g, 6.54 mmol), tert-butyl acetate (988 mg, 8.51 mmol), and toluene (15 mL). The resulting mixture was stirred at ambient temperature for 18 h then partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL). The organic layer was washed with brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 85:15, to give the title compound. MS: m/z=316 (M−C4H7).

Aufarbeitung

  1. customthen partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-4c43a41060b94d789bc27194f8068821
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

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