Tetrabutylammonium Fluoride → HCID 86727594, compound

Participants

Reaction Conditions

Reaction Steps

4-[7-(2-Fluoro-phenyl)-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.2 g, 0.320 mmol) was dissolved in tetrabutylammonium fluoride (1M in THF, 20 mL, 20.00 mmol) and the reaction mixture was heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature, quenched by the addition of water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic phase was washed with brine (2×30 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 7-50% EtOAc in petroleum ether) to give 4-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.086 g, 54%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.07 (brs, 1H), 7.40 (m, 1H), 7.36-7.29 (m, 1H), 7.22-7.09 (m, 2H), 6.96 (s, 1H), 6.62 (s, 1H), 4.75 (q, J=6.8 Hz, 1H), 4.60 (d, J=13.2 Hz, 2H), 3.26 (brs, 4H), 2.72 (brs, 4H), 1.57 (s, 3H), 1.45 (s, 9H).

Provenance & Evidence