Dichloromethane → 1-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1445940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445940
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][NH:13][C:12](=[O:17])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:20]Cl.F[B-](F)(F)F.C[O+](C)C>>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:17][CH3:20])[C:11]=2[CH:10]=[C:9]1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 591703201-Benzyl-2-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one

Produkt 1

HCID 591703081-benzyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridineAusbeute 35 %

Versuchsvorschrift

To a mixture of 1-benzyl-2-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridin-4-one (1) (3.48 g, 16.62 mmole) in dichloromethane (160 mL) trimethyloxonium tetrafluoroborate (4.52 g, 29.24 mmole) was added. The mixture was stirred at room temperature for 18 h. Additional trimethyloxonium tetrafluoroborate (2.25 g, 14.55 mmole) was added and stirred for 18 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (20:1 CH2Cl2:MeOH) to afford intermediate (2) Yield: 1.31 g, 35%.

Aufarbeitung

  1. additionwas added
  2. stirringstirred for 18 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (20:1 CH2Cl2:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-fd89634c8c6b4202afae1d74b0e995b2
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

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