tert-Butylsulfinamide, (R)-(+)- → HCID 86689830, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-acetylpyrrolo[3,2-b]pyridine-1-carboxylate (2.0 g, 7.68 mmol) and (R)-2-methylpropane-2-sulfinamide (1.04 g, 8.45 mmol) dissolved in anhydrous THF (50 mL) was added titanium (IV) ethoxide (3.2 mL, 15.37 mmol) at RT under a N2 atmosphere. The reaction mixture was stirred at 75° C. under N2 for 16 h. The solvent was removed in vacuo and the crude residue was diluted with EtOAc (ca. 100 mL). The reaction mixture was vigorously stirred while a saturated solution of brine (−20 mL) was added slowly. 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 in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/heptane to afford 1.50 g (53.7%) of (R)-tert-butyl 5-(1-(tert-butylsulfinylimino)-ethyl)-1H-pyrrolo[3,2-b]pyridine-1-carboxylate as yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.38 (d, J=8.6 Hz, 1H), 8.16 (d, J=8.8 Hz, 1H), 7.88 (d, J=3.8 Hz, 1H), 6.83 (d, J=3.8 Hz, 1H), 2.94 (s, 3H), 1.69 (s, 9H), 1.35 (s, 9H); MS (ESI) m/z: 364.3 [M+1]+.

Provenance & Evidence