Hydrochloric Acid → HCID 178479642, compound

Participants

Reaction Steps

According to the method of A57C and D, 3-((3-((E)-2-(pyridin-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-5-yl)methylene)indolin-2-one (13.1 mg, 0.026 mmol) was treated with boron trifluoride etherate, followed by 2 N HCl (water/EtOH) treatment. Suction filtration gave a solid which was rinsed with 1:1 EtOH:water (2×1 mL). Pumping under high vacuum gave an orange solid (7.3 mg, 69%, 55:45 mixture of E/Z isomers, HCl salt). 1H NMR (400 MHz, CD3OD) δ 9.83 (s, 0.4H), 8.73 (m, 2H), 8.59 (s, 0.6H), 8.33-8.20 (m, 3.5H), 7.95 (m, 1H), 7.91-7.87 (m, 1H), 7.80-7.63 (m, 3H), 7.25 (t, J=8.4 Hz, 1H), 7.07 (t, J=7.6 Hz, 0.4H), 6.96-6.87 (m, 1.6H); MS ESI 365.2 [M+H]+, calcd for [C23H16N4O+H]+ 365.14.

Provenance & Evidence