Tetrabutylammonium Fluoride → HCID 89662746, compound

Participants

Reaction Steps

A 1M solution of tetrabutyl-ammonium fluoride in THF (1.26 mL; 1.26 mmol; 1.2 eq.) was added to a cold (0° C.) solution of {2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethoxy]-phenyl}-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-methanone (540 mg; 1.05 mmol; 1 eq.) in THF (5 mL) and the resulting mixture was stirred at room temperature for 2.5 hours. After dilution with EA, the solution was washed with sat. aq. NaHCO3, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (50% EA in cyclohexane to EA) afforded the title compound (200 mg, 48%) as a white foam. 1H NMR (DMSO-d6) δ 7.52-7.36 (m, 1H), 7.37-7.23 (m, 1H), 7.23-7.14 (d, J=8.4 Hz, 1H), 7.09-6.96 (m, 1H), 4.96-4.73 (m, 3H), 4.55-4.38 (m, 2H), 3.51-3.37 (m, 2H), 2.84 (s, 1.5H), 2.80 (s, 1.5H), 2.62 (s, 1.5H), 2.55 (s, 1.5H), 1.24-1.11 (dd, J=6.2, 2.3 Hz, 2H). HPLC (max plot) 99.1%, Rt 3.35 min. UPLC/MS: (MS+) 401.2 ([M+H]+).

Provenance & Evidence