5-Bromo-2-phenyl-1,3-oxazole → 3-(2-Phenyl-oxazol-5-yl)-2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

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Reaction Steps

In a similar fashion to Example 1, react 5-bromo-2-phenyloxazole (Combi-Blocks; 120 mg, 0.52 mmol) with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5; 120 mg, 0.52 mmol) to provide the title compound (20 mg, 12%) as a white solid. MS ESI+ m/e 329 (M+1). 1H NMR (CDCl3) δ 8.78-8.70 (m, 1H), 8.05-7.99 (m, 2H), 7.95-7.89 (m, 1H), 7.82 (s, 1H), 7.81-7.70 (m, 1H), 7.50-7.41 (m, 3H), 7.30-7.25 (m, 1H), 4.31-4.21 (m, 2H), 3.38-3.24 (m, 2H), 2.82-2.66 (m, 2H). HPLC: 97.2%, Rt=16.67 min. TLC (SiO2): Rf0.3 (1:3 [80:18:2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Provenance & Evidence