Sodium Hydroxide → HCID 54579596, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-{4-[2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-piperidinyl}propanoate (D123) (200 mg, 0.481 mmol), 3-bromo-5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazole (D43) (161 mg, 0.481 mmol) and Pd(Ph3P)4 (55.6 mg, 0.048 mmol) was added tripotassium phosphate (307 mg, 1.444 mmol) under nitrogen. The solution was sealed for Biotage microwave irradiation at 120° C. for 20 min. To the resulted solution, Isopropanol (10 mL) and water (2 mL) and then sodium hydroxide (0.5 mL, 3.05 mmol) was added. This solution was stirred at 50° C. for 2 hr. The solution was neutralized with AcOH, dried, dissolved in DMF and purified by Mass Directed AutoPrep to afford 3-{4-[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]-1-piperidinyl}propanoic acid (E100) (40 mg).

Provenance & Evidence