5-Bromo-benzo[2,1,3]thiadiazole → 5-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]benzo[2,1,3]thiadiazole

Participants

Reaction Steps

In a similar fashion to Example 4, react 5-bromo-[2,1,3]-benzothiadiazole (Maybridge; 180 mg, 0.83 mmol) with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5; 190 mg, 0.83 mmol) to provide the title compound (65 mg, 16%) as a tan solid. Melting Range: 184-186° C. MS ESI+ m/e 320 (M+1). 1H NMR (CDCl3) δ 8.61-8.52 (m, 1H), 7.94 (s, 1H), 7.89-7.82 (m, 1H), 7.70-7.62 (m, 2H), 7.52-7.49 (m, 1H), 7.29-7.17 (m, 1H), 4.33-4.22 (m, 2H), 3.12-3.02 (m, 2H), 2.72-2.60 (m, 2H). HPLC: >99%, Rt=15.41 min. TLC (SiO2): Rf0.3 (1:1 [80:18-2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Provenance & Evidence