Methyl iodide → 1-(tert-Butyl-dimethyl-silanyl)-5-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a stirred and cooled (−78° C.) solution of bromide 4 (0.20 g, 0.64 mmol) in Et2O (2.5 mL) was added dropwise a 1.5 M solution of tert-BuLi in pentane (0.89 mL, 1.34 mmol). After 38 min MeI (0.1 mL, 1.61 mmol) was added dropwise and the mixture allowed to gradually warm to r.t. After 12 h the mixture was partitioned between CHCl3 and saturated aqueous NaHCO3 solution. The aqueous layer was extracted with CHCl3 (2×). The combined organic extracts were dried (MgSO4), and concentrated to afford 7 as a yellow oily residue, which was used directly in the next step without purification.

Provenance & Evidence