Sodium Carbonate → 6-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile

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Reaction Steps

A mixture of 6-bromo-imidazo[1,2-a]pyridine-7-carbonitrile (1.5 g, 6.8 mmol), 2,4-dichloro-benzeneboronic acid (1.9 g, 10.1 mmol), Pd(PPh3)4 (390 mg, 0.34 mmol) and Na2CO3 (2.0 M solution in water, 12 mL) in OME (30 mL) was refluxed for 14 h under an inert atmosphere of argon. The reaction mixture was cooled to RT, diluted in AcOEt (200 mL) and washed with water (200 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→1:1) to yield the title compound (750 mg, 2.6 mmol, 39%) as an orange foam. MS. 289 [M+1]+; HPLC: AtRet=1.50; TLC: RF 0.16 ([hexane/DCM 1:1]/TBME 3:7).

Provenance & Evidence