Methyl p-toluenesulfonate → HCID 86762621, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methylcarbamate (300 mg, 0.796 mmol) in anhydrous THF (30 mL) at 0° C. was slowly added NaH (60% in mineral oil, 48 mg, 1.194 mmol) and stirred at 0° C. for 30 min. To the mixture was added methyl 4-methylbenzenesulfonate (178 mg, 0.955 mmol) followed by stirring at RT for 18 h. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (2:1) to afford 232 mg (74.6%) of tert-butyl methyl((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)carbamate as a yellow solid. MS (ESI): m/z=392.2 [M+1]+.

Provenance & Evidence