4-Chloro-2-fluoro-5-nitrotoluene → 4-(5-chloro-2-methyl-4-nitrophenoxy)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Steps

Prepared from 1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-ol (0.150 g, 0.557 mmol; prepared as in Example 5, Step B) and 1-chloro-5-fluoro-4-methyl-2-nitrobenzene (0.106 g, 0.557 mmol), according to the procedure of Example 13, Step A. Purified by Biotage 40S column eluting with 3:1 hexane/EtOAc then EtOAc to obtain the product (184 mg, 75%) as an off white solid. 1H NMR (CDCl3, 400 MHz) δ 8.36 (d, J=5.1 Hz, 1H), 7.95 (s, 1H), 7.35 (d, J=9.0 Hz, 1H), 7.21 (s, 1H), 6.84 (d, J=8.6 Hz, 1H), 6.23 (d, J=5.1 Hz, 1H), 5.58 (s, 1H), 3.77 (s, 3H), 2.63 (s, 3H), 2.31 (s, 3H). LRMS (APCI pos) m/e 439 (M+1).

Provenance & Evidence