Tetrabutylammonium Fluoride → HCID 178517055, compound

Participants

Reaction Steps

A solution of 3-((3-(2-(pyridin-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazol-6-yl)methylene)indolin-2-one (57 mg, 0.115 mmol) in THF (3 mL) was treated with TBAF (0.58 mL of a 1.0 M solution in THF) and the reaction heated at reflux for 20 hours. The solvent was removed and the residue re-dissolved into EtOAc. The organics were washed with water (2×), brine (2×) and then dried (MgSO4). The solvent was removed and the residue purified by column chromatography (silica gel, 93:7 CH2Cl2/MeOH) to give a yellow solid which was impure by LC-MS. The mixture was further purified by prep-HPLC to give 11.3 mg, 27% of the title compound as a 76:24 mixture of (E)/(Z) geometric isomers. 1H NMR (400 MHz, CD3OD) δ 8.79, 7.87 (s, 1H), 8.69, 8.66 (d, J=6.52 Hz, 2H), 7.98-7.73 (m, 4H), 7.74, 7.62 (d, J=8.36 Hz, 1H), 7.66, 7.44 (d, J=8.44 Hz, 1H), 7.25, 7.05 (t, J=7.79 Hz, 1H), 6.95-6.84 (m, 2H), 3.53, 3.51 (s, 4H); MS ESI 367.2 [M+H]+, calcd for [C23H18N4O+H]+ 367.16.

Provenance & Evidence