tert-Butylsulfinamide, (R)-(+)- → HCID 86689869, compound

Participants

Reaction Conditions

Reaction Steps

To tert-butyl 5-acetyl-3-chloro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (2.90 g, 9.84 mmol) and (R)-2-methylpropane-2-sulfinamide (1.79 g, 14.76 mmol) dissolved in anhydrous THF (96 mL) was added titanium (IV) ethoxide (5.16 mL, 24.60 mmol) at RT under N2. The reaction mixture was then stirred at 75° C. under N2 for 16 h. Volatile solvent was removed under reduced pressure, and the crude residue was diluted with EtOAc (−250 mL). The reaction mixture was vigorously stirred while a saturated solution of brine (−40 mL) was slowly added. The reaction mixture was stirred for 15 min and filtered through a pad of Celite®. The organic layer from the filtrate was washed with water and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with EtOAc/heptane to afford 1.17 g (29.88%) of (R)-tert-butyl 5-(1-((tert-butylsulfinyl)imino)ethyl)-3-chloro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate and 2.06 g (56.59%) of (R)-ethyl 5-(1-((tert-butylsulfinyl)imino)ethyl)-3-chloro-1H-pyrrolo[3,2-b]pyridine-1-carboxylate.

Provenance & Evidence