HCID 59836036, compound → HCID 178489377, compound

Participants

Reaction Steps

3-[3-(2-Methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzonitrile (22 mg, 0.048 mmol) was dissolved in 1 mL trifluoroacetic acid. The mixture was stirred at room temperature for 1 h and the solvent was evaporated. The crude product was dissolved in 1 mL of methanol and 50 μL of ethylenediamine was added. After 15 min., mL of DMSO was added and the mixture was directly purified by mass-triggered preparative reverse phase HPLC to give 3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzonitrile as a colorless solid (4.6 mg, 30% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.90 (d, J=2.5 Hz, 1H), 8.44 (d, J=2.5 Hz, 1H), 8.28 (t, J=2 Hz, 1H), 8.12 (m, 2H), 7.84 (dt, J1=8 Hz, J2=1 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.64 (dd, J1=7.5 Hz, J2=2 Hz, 1H), 7.46 (m, 1H), 7.21 (d, J=8 Hz, 1H), 7.09 (td, J1=7.5 Hz, J2=1 Hz, 1H), 3.83 (s, 3H); MS: m/z 327 [MH+].

Provenance & Evidence