Hydrochloric Acid → HCID 86628683, compound

Participants

Reaction Steps

Add N-[1-isopropyl-3-(4-trimethylsilanylethynyl-phenyl)-1H-indol-6-yl]-methanesulfonamide (0.223 mmoles; 95.0 mg, prepared similarly to N-[1-isopropyl-3-(5-trimethylsilanylethynyl-pyridin-2-yl)-1H-indol-6-yl]-methanesulfonamide), dichloromethane (4.0 mL), methanol (4.0 mL); followed by Potassium Carbonate (1.119 mmoles; 154.6 mg) to a round bottom flask equipped with a stir bar. Stir the resulting material for 2 hours at room temperature. Dilute the reaction with water and acidify to pH of 6-7 with 1N HCl. Dilute the resulting aqueous mixture with brine and extract with dichloromethane. Concentrated the resulting mixture in vacuo and then purify the resulting material on a chromatotron (2MM silica gel plate; load CH2Cl2; run 30%-50% ethyl acetate gradient in hexanes) to obtain the desired product as a light-yellow crystalline solid, 50 mg (63%). MS (IS+) m/e 353.0 (M+1)

Provenance & Evidence