Methyl iodide → HCID 21743857, compound

Participants

Reaction Steps

A solution of 2,3-dimethyl-7-(2-phenyl-2-hydroxyethyl)pyrrolo[2,3-b]pyridine (as the base) (266 mg, 1.0 mmol) in 25 ml dry THF was deaerated and treated with 55% NaH dispersion in oil (48 mg, 1.1 mmol) for 30 min. Methyl iodide (62 μl, 1.0 mmol) was added and allowed to react for 50 min. The solvent was evaporated and the residue partitioned between 100 ml CH2Cl2 and 20 ml 5% NaOH. The organic layer was dried over MgSO4 and evaporated. The residue was chromatographed (silica, CH2Cl2 saturated with NH3). Pure fractions were pooled and evaporated leaving a gum which partly crystallized. Trituation with diethyl ether furnished 207 mg (65%) pure title compound.

Provenance & Evidence