Triisopropyl borate → [1-(Tert-butoxycarbonyl)-1H-pyrrolo[2,3-B]pyridin-2-YL]boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 1H-pyrrolo[2,3-b]pyridine-1-carboxylate (2.18 g, 10 mmol) and B(OiPr)3 (2.8 mL, 12.1 mmol) in 10 mL of THF cooled at 0° C. was added a LDA solution (16 mmol, prepared from 2.24 mL of iPr2NH, 15 mL of THF and 6.4 mL of 2.5 M n-BuLi solution in hexane) by a syringe pump over a period of 2 h. The reaction mixture was stirred for additional 1 h at 0° C. before being quenched by addition of 30 mL of pH 7 sodium phosphate buffer solution. The product was extracted with 2×100 mL of EtOAc. The extracts were dried over Na2SO4, filtered, and concentrated under vacuum to give 3 g of the title compounds as a gray solid which was used for the next step without further purification.

Provenance & Evidence