Triisopropyl borate → HCID 86634553, compound

Participants

Reaction Conditions

Reaction Steps

Triisopropyl borate (5.69 ml, 24.7 mmol) is added to a solution of N-(5-Bromo-2-chloro-pyridin-3-yl)-benzenesulfonamide (1 g, 2.87 mmol) in anhydrous THF (25 ml) under argon, and the resulting solution is cooled to −78° C. A 1.6 M solution of n-butyl lithium in hexanes (5.39 ml, 8.63 mmol) is added dropwise keeping the temperature below −70° C. The reaction is stirred at −78° C. for 50 minutes. The reaction is quenched with sat. aq. NaCl (20 ml) at −78° C. and then allowed to warm to room temperature and washed with EtOAc. The aqueous layer is concentrated in vacuo, and the residue is dissolved in 2.5M HCl, and the product is extracted into EtOAc, dried (MgSO4) and concentrated in vacuo to yield the title compound as a yellow oil. [M+H]+ 313.

Provenance & Evidence