Sodium hydride → 4-Bromo-1-(tert-butyl-dimethyl-silanyl)-7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine

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Reaction Steps

To a solution of 4-bromo-7-chloro-3-methyl-1H-pyrrolo[2,3-c]pyridine (1.07 g) in dry tetrahydrofuran (50 ml) at 0° C. under an atmosphere of nitrogen was added portionwise sodium hydride (60% dispersed in mineral oil, 384 mg). After addition, the solution was stirred at room temperature for 30 minutes. The solution was then recooled to 0° C. and a solution of tert-butyldimethylsilyl trifluoromethanesulphonate (2 ml) in dry tetrahydrofuran (10 ml) was added dropwise. The solution was stored at 5° C. overnight. The solution was partitioned between ethyl acetate and water and washed with water twice. The organic layer was dried (MgSO4) and evaporated to give a brown oil (2 g). The residue was used in the next step (d) without further purification.

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