4-Toluenesulfonyl chloride → HCID 86689845, compound

Participants

Reaction Steps

To a solution of 6-chloro-1H-pyrrolo[3,2-b]pyridine (5.0 g, 32.8 mmol) in THF (150 mL) in an ice bath was added NaH (1.57 g, 60% in mineral oil, 39.3 mmol). After stirring in an ice bath for 30 min, 4-toluenesulfonyl chloride (6.87 g, 36.1 mmol) was added. The mixture was stirred at RT overnight. The reaction mixture was quenched with water (50 mL) at 0° C. and extracted with EtOAc (300 mL). The extract was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc gradient (8:1 to 2:1) to afford 6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridine as a yellow solid (8.5 g, 84%). MS (ESI): m/z=307.0 [M+1]+.

Provenance & Evidence