2-Methyl-2-butene → HCID 86698783, compound

Participants

Reaction Steps

To a solution of crude 3-formyl-5-[4-(2-hydroxyethoxy)phenyl]-1H-indole-6-carbonitrile (110 mg, assume 0.2 mmol) in a mixture of THF (1.5 mL) and tert-butanol (1.5 mL) was added 2-methyl-2-butene (0.638 mL, 6.0 mmol) followed by a solution of sodium chlorite (169 mg, 2.0 mmol) and sodium phosphate monobasic monohydrate (284 mg, 2.06 mmol) in water (1.1 mL) via glass pipet at room temperature. The mixture was stirred at room temperature for 15.5 hours. The reaction mixture was poured into saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×8 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in DMSO (1.8 mL) and half of this solution was purified by reverse phase prep-HPLC to give the title compound (5 mg). MS (ES−) 321.1 (M−H)−. Retention time: 0.90 min Waters Xbridge dC18 5 um 4.6×50 mm, 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. (0.03% NH4OH). Flow: 2.0 mL/min.

Provenance & Evidence