Trimethyltin chloride → HCID 178454345, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of di-tert-butyl {4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-yl}imidodicarbonate (400 mg, 0.653 mmol) in anhydrous THF (10 mL) was added lithium diisopropylamide (2 M in THF, 1.6 mL, 3.3 mmol), and the mixture stirred for 30 minutes. Chlorotrimethylstannane (1 M in THF, 3.92 mL, 3.92 mmol) was added, and the mixture warmed to RT. The mixture was then cooled to −78° C., quenched by addition of glacial acetic acid (0.2 mL), and warmed to RT. The solution was adsorbed onto silica gel and purified by ISCO chromatography (10 to 20% EtOAc:heptane) to afford 347 mg (69%) of the title compound as a tan solid. 1H NMR (400 MHz, CDCl3): δ 0.10 (s, 6 H), 0.45 (s, 9 H), 0.92 (s, 9 H), 1.39 (s, 18 H), 1.50-1.62 (m, 2 H), 1.87-2.09 (m, 4 H), 2.24 (d, J=12.1 Hz, 2 H), 3.69-3.80 (m, 1 H), 4.21 (tt, J=11.5, 3.9 Hz, 1 H), 7.08-7.11 (m, 1 H), 7.78 (s, 1 H), 7.88-7.91 (m, 1 H), 8.31 (s, 1 H).

Provenance & Evidence