Sodium Carbonate → 3-{5-[(2-Cyclohexylethylamino)methyl]pyridin-2-yl}-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (Preparation 18, 150 mg, 0.57 mmol) and (6-bromopyridin-3-ylmethyl)-(2-cyclohexylethyl)amine (Preparation 15, 188 mg, 0.63 mmol) in dioxane (3 mL) was added 2M Na2CO3 (1 mL) and bis(diphenylphosphinoferrocene)-palladium dichloride (47 mg, 0.06 mmol). The mixture was purged with argon for 10 min and the mixture heated to 70° C. for 6 h. On cooling to rt, EtOAc (50 mL) was added and the organic phase washed with water (2×30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (0.4% NH3: 4% MeOH: DCM) to give the title compound: RT=2.53 min; m/z (ES+)=352.2 [M+H]+.

Provenance & Evidence