Hydrochloric Acid → Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Participants

Reaction Steps

To a solution of 11.2 mmol of N-t-butylbenzenesulfonamide (from Step C) in anhydrous THF (20 mL) cooled to -40° C. under N2 was addeel 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to room temperature and stirred for 2 hours. To the mixture, containng the dianion at 0° C., was added triisopropyl borate (3.9 mL, 1.5 equiv). The next day, 2 N HCl (3 mL) was added and the mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic solution was washed with 2N HCl, H2O and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. The material was used in the next step without further purification.

Provenance & Evidence