Reaktion #71549

Reaktionsgleichung

1-benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde

Compound 14

1-benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde

NaClO2

→

title compound

1-Benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid

Lösungsmittel

t-BuOH

2-methyl-2-butene

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with EtOAc (×2)
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 chromatography on silica gel (0→100% EtOAc-hexanes

Vorschrift

To a solution of 1-benzyl-6-chloro-2-isopropyl-1H-pyrrolo[3,2-c]pyridine-3-carbaldehyde (Compound 14, 146 mg, 0.47 mmol) in t-BuOH (15 ml) and 2-methyl-2-butene (10 ml) was added a solution of NaH2PO4 (1.41 g, 11.8 mmol) and NaClO2 (80%, 1.05 g, 9.3 mmol) in H2O (10 ml). The mixture was stirred at room temperature for 16 h and was extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes, then 0→30% MeOH—CH2Cl2) to yield the title compound as a yellow solid.

Quelle