Dichloromethane → HCID 53874238, compound

Participants

Reaction Steps

A solution of 2,3-dimethylpyrrolo[2,3-b]pyridine (554 mg, 3.8 mmol) and o-bromophenethyl bromide (1000 mg, 3.8 mmol) in 11 ml CH3CN was refluxed for 16 h. The solvent was evaporated and the residue chromatographed (silica, CH2Cl2 /MeOH; 9/1) to give 546 mg enriched product. Pure 2,3-dimethyl-7-(o-bromophenethyl) pyrrolo[2,3-b]pyridine was obtained by a second chromatography (silica, CH2Cl2 saturated with NH3/petroleum ether; 7/3). A deaerated solution of 2,3-dimethyl-7- (o-bromophenethyl) pyrrolo[2,3-b]pyridine (249 mg, 0.76 mmol) in 25 ml dry THF was cooled to -78° C. and treated with 1.6M n-BuLi in hexane (576 μl, 0.91 mmol). After 3 min a vigurous stream of CO2 (g) was bubbled through the solution. The solution was allowed to warm to room temperature and 1.5 ml H2O was added. The solvent was evaporated and the residue chromatographed (reversed phase silica, MeOH/H2O; 6/4) yielding 51 mg (23%) pure amino acid.

Provenance & Evidence