N-Iodosuccinimide → 2-(2-Chlorophenyl)-3-(4-chlorophenyl)-7-iodomethyl-6,7-dihydro-8-oxa-1,4,8b-triaza-as-indacene

Participants

Reaction Steps

To a mixture of 6-allyl-3-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidin-7-ol (I-15A-1a; 25 mg, 0.063 mmol) in 9:1 methylene chloride/chloroform (0.63 ml) at 0° C. was added N-iodosuccinimide (15 mg, 0.066 mmol), portionwise. The reaction was stirred overnight at room temperature and then extracted from water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo. Purification on a Biotage™ Flash 12S column using 20% ethyl acetate in hexanes as eluant afforded compound 15A-1 (15 mg, 46%) as a solid: +ESI MS (M+1) 522.3; 1H NMR (400 MHz, CD3OD) δ 8.46 (s, 1H), 7.53–7.40 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.45–5.41 (m, 1H), 3.81–3.64 (m, 2H), 3.33 (d, J=6.2 Hz, 2H).

Provenance & Evidence