Dichloromethane → 7-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-imidazo[1,2-a]pyridine

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Reaction Conditions

Reaction Steps

Combine 7-chloro-imidazo[1,2-a]pyridine (PCT Appl. WO 01/38326 A2; 134 mg, 0.88 mmol) with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5; 369 mg, 0.97 mmol) in the presence of tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.03 mmol) and 2M aqueous sodium bicarbonate (1.0 mL) in benzene (2.1 mL) and ethanol (0.3 mL). Heat the mixture for 67 h at 100° C. Dilute the reaction with methylene chloride (10 mL) and water (10 mL). Separate the layers and extract the aqueous layer with methylene chloride (2×10 mL). Combine the organic layers and dry over sodium sulfate. Filter the solution and evaporate the solvent. Purify the crude product by flash chromatography using the appropriate ammonia in methanol/methylene chloride mixture to give the title compound as a tan solid (41 mg, 15%). MS m/e (302.0, M+1). 1H NMR (CDCl3) δ 8.57 (m, 1H), 7.96 (dd, J=1, 7 Hz, 1H), 7.6 (m, 5H), 7.19 (m, 1H), 6.69 (dd, J=1, 7 Hz, 1H), 4.27 (t, J=8 Hz, 2H), 3.08(t, J=7 Hz, 2H), 2.71 (q, J=7 Hz, 2H).

Provenance & Evidence