Cesium carbonate → HCID 178509957, compound

Participants

Reaction Steps

In a manner identical to that described above for the synthesis of 1-2, from 2.97 g (10.68 mmol) of 3-chloro-5-(2-chloro-5-hydroxyphenoxy)benzonitrile (C-3), 3.29 g (10.15 mmol) of Cs2CO3, and 3.34 g (10.15 mmol) of tert-butyl 3-(bromomethyl)-6-fluoro-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (37-5) was prepared crude 3-chloro-5-{2-chloro-5-[(1-t-butyloxycarbonyl-6-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)methoxy]phenoxy}benzonitrile (37-6) as an oil. This BOC-protected material (3.66 g) was immediately dissolved in 10 mL TFA, and the resulting solution stirred for 20 minutes at room temperature. The crude reaction mixture was concentrated in vacuo and purified via silica gel chromatography (10-70% EtOAc/hexane) to yield the title compound. H1 NMR (CDCl3): 5.47 (s, 2H), 6.85 (d, 1H), 6.95 (d, 1H), 7.02 (s, 1H), 7.10 (s, 1H), 7.30 (s, 1H), 7.40 (d, 1H), 8.38 (t, 1H), 11.38 (bs, 1H).

Provenance & Evidence