N,N,N',N'-Tetramethylethylenediamine → {1-[tert-Butyl(dimethyl)silyl]-5-fluoro-1H-indol-4-yl}boronic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of the product of Step 1 (4.98 g, 20 mmol) and TMEDA (2.32 g, 20 mmol) in THF at −78° C. was slowly added a 1.3M solution of s-BuLi (15.4 mL, 20 mmol) in cyclohexane and the mixture was stirred for 2 h at −78° C. Triisopropyl borate (3.76 g, 20 mmol) was added to the mixture at −78° C. and stirred for another 1 h and then warmed to −20° C. Water was added and the mixture was extracted with EtOAc and the organic layer was dried over Na2SO4 and evaporated. The residue was re-crystallized (EtOAc and n-hexane) to give the title compound (1.2 g, 20.7%).

Provenance & Evidence