Hydrochloric Acid → Ethyl 2-(4-chloro-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 1.85 mmol) in DMF (5 mL) was added Cs2CO3 (1.51 g, 4.62 mmol) at room temperature, followed by 2-chloropyrazine (254 mg, 2.22 mL). The resulting mixture was stirred at 90° C. for 40 min. The mixture was poured into ice-water and acidified to pH=2 with diluted hydrochloric acid. The resulting mixture was extracted with EtOAc (2×25 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to give the product (110 mg, yield: 32%). MS (ESI) m/z=349 [M+H]+.

Provenance & Evidence