Triethylsilane → HCID 71514779, compound

Participants

Reaction Steps

The above (S)-tert-butyl 1-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-vinylpyridin-2-yl)piperidin-3-ylcarbamate (23.7 mg, 0.038 mmol) was dissolved in Trifluoroacetic Acid (2 mL) and Methylene chloride (2 mL). To the solution was add Trifluoromethanesulfonic acid (50 uL, 0.6 mmol) and Triethylsilane (30 uL, 0.19 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was then concentrated, and the residue was purified by reverse phase HPLC to afford 307 as an off-white solid (5.1 mg, 34%). 1H NMR (400 MHz, DMSO) δ 9.32 (d, J=1.9 Hz, 1H), 9.20 (s, 1H), 9.11 (s, 1H), 8.59 (d, J=3.8 Hz, 1H), 8.46 (d, J=8.0 Hz, 1H), 7.96 (d, J=7.9 Hz, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.52 (dd, J=8.0, 4.7 Hz, 1H), 6.80 (dd, J=17.7, 11.0 Hz, 1H), 5.88 (d, J=17.6 Hz, 1H), 5.38 (d, J=11.3 Hz, 1H), 3.77 (d, J=9.7 Hz, 1H), 3.58 (d, J=12.1 Hz, 1H), 2.92-2.82 (m, 2H), 2.82-2.72 (m, 1H), 1.95 (d, J=12.7 Hz, 1H), 1.87-1.71 (m, 2H), 1.25 (dd, J=19.0, 10.7 Hz, 1H); ESI MS m/z=398.2 (M+1)

Provenance & Evidence