1H-Pyrrolo(2,3-b)pyridine → HCID 178526243, compound

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Reaction Steps

7-Azaindole (commercially available from Aldrich) (Intermediate C1) (31 mmol) in THF (70 mL) was reacted with MCPBA: 3-chloroperoxybenzoic acid (˜35 mmol) at rt for 18 h. The solvent was removed under reduced pressure and partitioned between 2N NaOH and ethyl acetate. The product was extracted multiple times with ethyl acetate and the layers were combined, dried over Na2SO4, filtered, and reduced under vacuum. The residue was purified by column chromatography on SiO2 6% NH3-MeOH in CH2Cl2 to yield 1H-pyrrolo[2,3-b]pyridine 7-oxide (Intermediate C2) (34%) (see: Minakata, S. et. aL Synthesis 1992, 661. ). 1H-pyrrolo[2,3-b]pyridine 7-oxide (Intermediate C2) (8.95 mmol) in THF (60 mL) was treated with hexamethyldisilazane (HMDS): (90 mmol) and a dropwise addition of benzoylchloride (22.5 mmol). The mixture was allowed to stir at rt for 1 h. The mixture was diluted with sat. NaHCO3 and the aqueous layer extracted with ethyl acetate. The organic layers were combined, dried over MgSO4, filtered and freed of solvent. The residue was purified by column chromatography (10% EtOAc:hexane) to give the product 6-chloro-pyrrolo[2,3-b]pyridin-1-yl-phenyl-methanone (Intermediate C3) as a solid.

Provenance & Evidence