Methyl iodide → 4-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

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Reaction Conditions

Reaction Steps

To a stirring solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (20.08 g) in anhydrous Tetrahydrofuran (200 ml) at −50° C. was added LDA (66.2 ml) dropwise over 20 min. The resulting suspension was stirred at −50° C. for 1 h then methyl iodide (22.34 ml) was added dropwise over 20 min. The reaction mixture was stirred at −30° C. for 1 h then quenched by the addition of water. The layers were separated and the aq was re-extracted with DCM. The THF layer was concentrated in vacuo then re-dissolved in DCM. The DCM extracts were then combined and washed with water, brine, then dried over magnesium sulfate, filtered and evaporated to yield an oily residue that was recrystallised using cyclohexane:ethyl acetate (5:1) to yield a solid which was triturated using methanol, collected by filtration then dried in vacuo at 45° C. overnight to yield the title compound, 10.52 g as a pale yellow solid.

Provenance & Evidence