HCID 117667619, compound → HCID 117667801, compound

Participants

Reaction Steps

To a cooled (0° C.) suspension of 6-(5-formyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (125 mg, 0.37 mmol) in THF (1 mL) is added a solution of isopropylmagnesium chloride in THF (1.3M, 850 μL, 1.1 mmol). The resultant mixture is stirred warming to room temperature for 3 h. The reaction is quenched with saturated aqueous ammonium chloride solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is taken up in MeOH (1 mL) and 4N HCl in 1,4-dioxane (1 mL) is added. The reaction is stirred at room temperature for 16 h then is concentrated to provide 2-methyl-1-[5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-propan-1-ol (124 mg) as the dihydrochloride salt.

Provenance & Evidence