Water → HCID 86628337, Verbindung

HRID 21338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21338
[Br:1][C:2]1[N:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])=[O:5].[Li+].CC([N-]C(C)C)C.CCCCCCC.C1C[O:38][CH2:37]C1.C(C1C=CC=CC=1)C.CN(C=O)C.O>C1COCC1>[Br:1][C:2]1[C:3]2[C:4](=[O:5])[N:6]([C:7]([CH3:15])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:8])[CH:37]([OH:38])[C:16]=2[CH:17]=[CH:18][N:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 86590273LDA THF ethylbenzene heptaneHCID 866283362-bromo-N-(1-methyl-1-phenylethyl)nicotinamide

Produkt 1

HCID 86628337HCID 86628337, VerbindungAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Bromo-N-(1-methyl-1-phenylethyl)nicotinamide (500 mg, 1.57 mmol) was dissolved in THF (20 mL), and the solution was added with LDA-heptane/THF/ethylbenzene solution (2.0 mol/L, 3.5 mL, 7.1 mmol) by drops at −78° C. for 25 minutes under argon atmosphere, followed by stirring at the same temperature for 1.6 hours. Then, the mixture was added with DMF (0.267 mL, 3.45 mmol) and warmed from −78° C. to room temperature over 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3) to obtain 4-bromo-1-hydroxy-2-(1-methyl-1-phenylethyl)-1,2-dihydropyrrolo[3,4-c]pyridine-3-one (138 mg, yield 25%).

Aufarbeitung

  1. temperaturewarmed from −78° C. to room temperature over 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash column chromatography (chloroform/methanol=100/1 to 97/3)

Quellen und Nachweise

ORD-Eintrag
ord-cda688a316bd420eb4294ebce63fa3f3
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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