1,2-Dichloroethane → 3-Fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoic acid (0.222 g, 0.569 mmol) in 1,2-dichloroethane (1.5 mL, 19 mmol) and acetonitrile (1.5 mL, 29 mmol) under argon were added chlorosulfonyl isocyanate (0.074 mL, 0.853 mmol) and triethylamine (0.12 mL, 0.853 mmol). The reaction mixture was stirred at 90° C. for 18 h. The cooled reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 solution and brine; dried (MgSO4). ISCO purification (with 10% to 50% EtOAc/hexanes) afforded 3-fluoro-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)benzonitrile as an off-white solid. MS (ESI) m/z: Calculated: 371.1; Observed: 372.0 (M++1).

Provenance & Evidence