Sodium Hydroxide → HCID 19008909, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[5-(2-butyl-imidazo[4,5-b]pyridin-3-yl)-naphthalen-2-yl]-benzoic acid methyl ester (40 mg) in EtOH (1.0 mL) at room temperature was added 2N NaOH (0.5 mL). The reaction mixture was heated at 50° C. for 17 hours. The cooled solution was concentrated in vacuo. The residue was diluted with saturated aqueous NaCl (10 mL) and neutralized with concentrated HOAc. The aqueous solution was extracted with CHCl3 (3×30 mL). The combined extracts were dried MgSO4) and concentrated in vacuo. The residue was azeotroped with heptane (30 mL) and diluted with EtOAc (1 mL) and hexanes (15 mL). The solid that precipitated was filtered and dried. 1H NMR (250 MHz, d6 -DMSO): d 8.15 (m, 4 H), 7.72 (m, 3 H), 7.46 (m, 4 H), 7.30 (dd, 1 H), 6.94 (d, 1 H), 2.63 (m, 2 H), 1.63 (m, 2 H), 1.25 (m, 2 H), 0.74 (t, 3 H).

Provenance & Evidence