Reaktion #71543

Reaktionsgleichung

1-benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

Compound 7

1-benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde

NaClO2

NaClO2

→

title compound

1-Benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

Lösungsmittel

t-BuOH

2-methyl-2-butene

H2O

H2O

2-methyl-2-butene

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction mixture was extracted with EtOAc (×3)
2. 2
   Waschenthe combined organic layer was washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes)

Vorschrift

To a solution of 1-benzyl-2-isopropyl-5-methoxy-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (Compound 7, 20 mg, 0.065 mmol) in t-BuOH (1.5 ml) and 2-methyl-2-butene (1 ml) was added a solution of NaH2PO4 (94 mg, 0.78 mmol) and NaClO2 (80%, 73 mg, 0.65 mmol) in H2O (1.5 ml). The mixture was stirred at room temperature and additional 2-methyl-2-butene and a solution of NaH2PO4 and NaClO2 in H2O were added at the above ratio every 6-16 h until the progress of the reaction was satisfactory. The reaction mixture was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (PTLC) on silica gel (50% EtOAc-hexanes) to yield the title compound.

Quelle