5-Indolylboronic acid → 5-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-1H-indole

Participants

Reaction Steps

In a similar fashion to Example 1, react 1H-indole-5-boronic acid (Fluka; 150 mg, 0.95 mmol) with 3-bromo-2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (Preparation 4; 250 mg, 0.95 mmol) to provide the title compound (10 mg, 4%) as an off-white solid. MS ESI+ m/e 301 (M+1). 1H NMR (CDCl3) δ 8.67-8.58 (m, 1H), 7.61 (s, 1H), 7.52-7.45 (m, 1H), 7.39-7.29 (m, 2H), 7.21-7.16 (m, 1H), 7.14-7.04 (m, 2H), 6.52-6.48 (m, 1H), 4.31-4.21 (m, 2H), 3.06-2.98 (m, 2H), 2.73-2.60 (m, 2H). TLC (SiO2): Rf 0.4 (1:3 [80:18:2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Provenance & Evidence