Cesium fluoride → (r)-3-(2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenoxy)propane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenol (35.1 mg, 94 μmol) and cesium fluoride (0.72 mg, 4.7 μmol) in anhydrous DMF (0.5 mL) was stirred at 25° C. for 1 h. (R)-(+)-glycidol (98% ee) (6.6 μl, 99 μmol) was then added, and the resulting mixture was heated under argon at 80° C. for 2 d. Additional (R)-(+)-glycidol (6.56 μl, 98.9 μmol) was then added, and the reaction mixture was heated at 80° C. for 18 h. The reaction mixture was subsequently cooled to 25° C., filtered through Celite, diluted with DMSO (1.5 mL), and purified by rpHPLC (10-100% CH3CN/water+0.1% TFA) to provide (R)-3-(2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenoxy)propane-1,2-diol as a white solid. MS (ESI) m/z: Calculated: 446.2; Observed: 447.0 (M++1).

Provenance & Evidence