2-Methyl-2-butene → HCID 71767832, compound

Participants

Reaction Steps

To a solution of 6-chloro-5-[2-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carbaldehyde (57 mg, 0.17 mmol) in acetonitrile (1 mL) and tert-butanol (1 mL) was added a solution of sodium chlorite (112 mg, 1.7 mmol), sodium phosphate monobasic hydrate (199 mg, 1.7 mmol) in water (2 mL) and 2-methyl-2-butene (0.72 mL, 6.8 mmol). The mixture was stirred at room temperature for 24 hours. The mixture was concentrated in vacuo and treated with ethanol. The solids were filtered and the filtrate was concentrated in vacuo to give crude product, which was purified using reverse phase chromatography to give the title compound (12 mg, 20%). MS (ES+) 360.057 (M+H)+. Retention time: 2.60 min. Column: Waters Atlantis dC18 4.6×50 mm, 5 μm. Modifier: TFA 0.05%. Gradient: 95% H2O/5% MeCN linear to 5% H2O/95% MeCN over 4.0 min, HOLD at 5% H2O/95% MeCN to 5.0 min. Flow: 2.0 mL/min.

Provenance & Evidence