Acetic Acid → 1,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one

HRID 641366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641366
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12]Br.[CH3:14][Si:15]([CH3:31])([CH3:30])[CH2:16][CH2:17][O:18][CH2:19][N:20]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:23]2[CH2:22][C:21]1=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(=O)C>CN(C=O)C>[N+:9]([C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][CH:7]=1)[CH2:2][C:22]1([C:23]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:20]([CH2:19][O:18][CH2:17][CH2:16][Si:15]([CH3:30])([CH3:14])[CH3:31])[C:21]1=[O:29])[CH2:12]2)([O-:11])=[O:10]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 108523601,2-Bis(bromomethyl)-4-nitrobenzene2×HCID 574588861-((2-(Trimethylsilyl)ethoxy)methyl)-1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one2×

Produkt 1

HCID 591667381,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1,2-bis(bromomethyl)-4-nitrobenzene (40.9 g, 132 mmol, described in Intermediate 2) and 1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (31.5 g, 119 mmol, described in Intermediate 1) in DMF (2 L) was added cesium carbonate (129 g, 397 mmol), portionwise, over 5 min. After 18 h, acetic acid (7.6 mL) was added and the mixture was concentrated to a volume of about 500 mL, then partitioned between EtOAc (1.5 L) and H2O (1 L). The organic layer was washed with H2O (1 L), then brine (500 mL), then dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=412 (M+1).

Aufarbeitung

  1. waitAfter 18 h
  2. concentrationthe mixture was concentrated to a volume of about 500 mL
  3. custompartitioned between EtOAc (1.5 L) and H2O (1 L)
  4. washThe organic layer was washed with H2O (1 L)
  5. dry with materialbrine (500 mL), then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-df9616ad921546acaaa71cda38d355a3
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696192B2

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