Methyl iodide → HCID 58505629, compound

Participants

Reaction Steps

To a stirred solution of ethyl 3-{3-[(4-bromophenyl)carbamoyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoate (100 mg, 0.18 mmol) in DMF (2 mL) is added NaH (60% dispersion in mineral oil, 7.7 mg, 0.19 mmol) at 0° C. The suspension is stirred for 10 minutes then iodomethane (12.0 μl 0.19 mmol) is introduced and the reaction mixture is stirred overnight. The mixture is quenched with water, extracted with EtOAc, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, hexanes to 40% EtOAc in hexanes) gives ethyl 3-{3-[(4-bromophenyl)(methyl)carbamoyl]-1-(2,2-dimethylpropanoyl)-7-(propan-2-yl)indolizin-2-yl}-2,2-dimethylpropanoate (75 mg, 73%) that is dissolved in THF (8 mL), MeOH (1 mL), and water (1 mL) and treated with 10M aqueous NaOH (0.1 mL). The mixture is stirred for 16 h then concentrated and acidified with HOAc. The resulting solid is filtered, washed with water, collected, and dried to give the title compound (50 mg, 70%).

Provenance & Evidence