2-Aminopyridine → HCID 178461249, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1) (0.5 g, 1.128 mmol) in toluene (5 mL) in a pyrex tube, 2-aminopyridine (0.127 g, 1.35 mmol), and BINAP (35 mg, 0.056 mmol) were added, and the reaction mixture was degassed with argon for 5 minutes. Pd2(dba)3 (51 mg, 0.056 mmol) and potassium tert-butoxide (0.189 g, 1.69 mmol) were added, and the tube was capped and heated to 100° C. for 17 h. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure, The residue was dissolved in ethyl acetate (20 mL), washed with water (5 mL) and brine (5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on a silica gel column using 40% ethyl acetate/petroleum ether as eluent to give 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-(pyridin-2-ylamino)-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ES/APCl calc'd. for C25H24ClN7 [M+H]+ 458. found 458.

Provenance & Evidence