HCID 86610107, compound → HCID 178509911, compound

Participants

Reaction Steps

A solution of 250 mg (0.50 mmol) of tert-butyl-3-{[4-chloro-3-(3-chloro-5-cyanophenoxy)phenyl]ethynyl}-1H-pyrazolo[3,4-]pyridine-1-carboxylate in 10 mL of absolute EtOH was hydrogenated at 1 atm pressure (balloon) over 250 mg of 10% Pd on carbon catalyst. After approximately 24 hours, the reaction mixture was filtered through a pad of Celite, and the filtrate concentrated in vacuo to a yellow oil. The crude intermediate oil was dissolved in 1 mL TFA, and the solution stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo to provide the crude product as a dark oil. The dark oil was purified by reversed phase preparative LC on a Gilson apparatus to give the desired product as a fluffy off-white solid. MS M+=409. 1H NMR (CDCl3): 3.17 (t, 2H), 3.31 (t, 2H), 6.94 (m, 2H), 7.09 (m, 2H), 7.15 (q, 1H), 7.32 (t, 1H), 7.39 (d, 1H), 7.80 (dd, 1H), 8.54 (dd, 1H), 10.5-11.5 (very br, 1H).

Provenance & Evidence