Hydrochloric Acid → HCID 59805742, compound

Participants

Reaction Conditions

Reaction Steps

5-Hydroxy-1-methyl-1H-indole-3-carbaldehyde (I-2) (0.5 g, 2.86 mmol), 2-Bromo-acetamide (0.43 g, 3.1 mmol), and N′″-tert-butyl-N,N,N′,N′,N″,N″-hexamethyl-phosphorimidic triamide (2.18 mL, 8.6 mmol) were dissolved into anh. DMF (3 mL) in a seal tube. The resulting solution was then sealed and heated at 120° C. (monitored by LCMS). The reaction completed after 3.5 h. The mixture was cooled to room temperature, added 20 mL of water, and 6 N HCl to pH 2-3. The mixture was then extracted with ethyl acetate (20 mL×6). The organic layers were combined, washed with brine (10 mL×2), dried over Mg2SO4, filtered and dried under reduced pressure to give the title compound as 0.5 g orange powder (crude yield: 76%, used without further purification). LCMS (2-85% ACN/H2O in 7 min): M+ 233.1 (100%); 95% purity (at 220 nM).

Provenance & Evidence