2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a stirred solution of the crude azaindoline 7 (0.64 mmol) in CH2Cl2 (10 mL) was added DDQ (145 mg, 0.64 mmol) in one portion. After 20 min the resulting black mixture was diluted with saturated aqueous NaHCO3 solution and stirred vigorously for 15 min. The aqueous layer was extracted with CHCl3 (2×) and the combined organic solutions were dried (MgSO4), filtered and concentrated to afford azaindole 8 as a brown oil, which was used directly in the next step without purification.

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