Tetrabutylammonium Fluoride → HCID 178517043, compound

Participants

Reaction Steps

A mixture of (E)-3-((3-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)methylene)indolin-2-one (47 mg, 0.11 mmol) and tetrabutylammonium fluoride (1.0 M in THF, 10 mL, 10 mmol) in anh. THF (30 mL) was refluxed under Ar for 18 h. The reaction mixture was then concentrated to a brown oil, which was diluted with H2O, extracted (2% MeOH in DCM), washed (H2O (2×), brine), dried (Na2SO4, and MgSO4) and concentrated under reduced pressure. The material was suspended in DCM, collected by filtration and washed with xs. DCM to afford the title compound as a yellow solid (7.0 mg, 21%). 1H NMR (400 MHz, CD3OD) δ ppm 7.90 (d, J=8.53 Hz, 1H), 7.86 (s, 1H), 7.78 (s., 1H), 7.65 (d, J=8.03 Hz, 1H), 7.42 (d, J=8.78 Hz, 1H), 7.23 (t, J=8.03 Hz, 1H), 6.92 (d, J=7.78 Hz, 1H), 1H), 6.87 (t, J=7.65 Hz, 1H), 2.26-2.36 (m, 1H), 1.04-1.11 (m, 4H); MS ESI 302.1 [M+H]+, calcd for [C19H15N3O+H]+ 302.3.

Provenance & Evidence