Azidotrimethylsilane → HCID 178463396, compound

Participants

Reaction Conditions

Reaction Steps

9-ethynyl-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (150 mg, 0.47 mmol) was dissolved in DMF/MeOH (2.0 mL) in a sealed tube. To the solution was added CuI (5.0 mg, 0.020 mmol) and azidotrimethylsilane (270 mg, 2.4 mmol) under an argon atmosphere. The mixture was stirred at 100° C. in a sealed tube for 8 h. The resulting solution was diluted with water (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, filtered, and purified by preparative TLC to afford 9-(1H-1,2,3-triazol-4-yl)-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (400 MHz, MeOD) δ 10.28 (s, 1H), 8.38 (d, J=8.4 Hz, 2H), 8.30 (d, J=6.4 Hz, 1H), 7.38 (d, J=7.2 Hz, 1H), 6.64 (d, J=7.2 Hz, 1H), 4.78 (m, 1H), 1.28 (d, J=6.8 Hz, 3H), 1.04 (s, 9H). LRMS calculated for C20H22N6O [M+H]+, 363; found 363.

Provenance & Evidence