Sodium Carbonate → 6-(2,4-Dichloro-phenyl)-3-(6-fluoro-pyridin-3-yl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile

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Reaction Conditions

Reaction Steps

In a sealed tube, a mixture of 3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile (115 mg, 0.25 mmol), 2-fluoro-5-pyridine-boronic acid (38.4 mg, 0.27 mmol), PdCl2(PPh3)2 (8.7 mg, 0.01 mmol) and Na2CO3 (2.0 M solution in water, 0.43 mL) in DME (1 mL) was heated at 150° C. for 17 min in a microwave oven. The reaction mixture was cooled to RT, diluted in AcOEt (20 mL) and washed with water (2×10 mL). The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/TBME 95:5→7:3) to yield the title compound (64 mg, 0.14 mmol, 56%) as a white solid. MS: 455 [M+1]+; HPLC: AtRet=3.14; TLC: RF 0.34 (hexane/TBME 1:1).

Provenance & Evidence