N-bromobutanimide → 3-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one

HRID 2389391

Reaktionsgleichung

Reaktionsgleichung von HRID 2389391
[CH3:1][C:2]1([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[Br:19]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1([CH2:12][C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:19])[CH:9]=2)[NH:4][C:3]1=[O:11]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 594437543-methyl-3-(pyrimidin-5-ylmethyl)-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 252556843-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-Methyl-3-(pyrimidin-5-ylmethyl)-1,3-dihydro-2H-indol-2-one (900 mg, 3.76 mmol) and N-bromosuccinimide (669 mg, 3.76 mmol) in N,N-dimethylformamide (20 mL) were stirred at room temperature for 3 days. The mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC on Chiralpak AS, eluting with 25% isopropyl alcohol/CO2, to afford the enantiomers of 3-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one. Enantiomer A was isolated as a white solid.

Aufarbeitung

  1. washwashed with water (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC on Chiralpak AS,
  6. washeluting with 25% isopropyl alcohol/CO2

Quellen und Nachweise

ORD-Eintrag
ord-09ab891bd8c64b2896d066c0de5b1620
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273749B2

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