Acetic Acid → HCID 67003710, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask equipped with a reflux condenser was charged with 3-(5-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)azetidin-3-ol (100 mg, 0.225 mmol) (Example 103A), paraformaldehyde (33.8 mg, 1.125 mmol), dichloroethane (2.5 mL), and acetic acid (0.064 mL, 1.125 mmol). Sodium cyanoborohydride (0.059 ml, 1.125 mmol) was added in three portions, and the mixture heated to 90° C. for 1 hour. The reaction mixture was slowly cooled to room temperature, and then to 0° C. in an ice-bath. Saturated sodium bicarbonate solution was added, and the mixture stirred vigorously for about an hour. The layers were separated, and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to give the title compound. MS APCI(+) m/z 459.24 (M+H)+.

Provenance & Evidence