2-Amino-4-(trifluoromethyl)pyridine → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

Participants

Reaction Steps

To the stirred solution of 2-amino-4-(trifluoromethyl)pyridine (10.79 g, 66.6 mmol) and 4-dimethylaminopyridine (7.39 g, 60.5 mmol) in Acetonitrile (125.00 ml) was added a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl chloride (16.12 g, 60.50 mmol) in Acetonitrile (75.00 ml) dropwise at room temperature. The solution turned into suspension after about half an hour and was stirred at r. t. overnight. The reaction mixture was concentrated and partitioned between 250 ml 0.2 N HCl and 250 ml CH2Cl2. The organic phase was separated and washed with 2×250 ml 0.2N HCl. The organic phase was dried over MgSO4 and evaporated to dryness. The crude was purified on RediSep 220 g silica cartridge and eluted with 1 lt Hexane, 4 lt 10% EtOAc/Hexane, 4 lt 20% EtOAc/Hexane gave white solid product 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide. 1HNMR (CD3Cl, 500 MHz, δ): 8.83 (1H, br), 8.71 (1H, s), 8.45 (1H, d), 7.93 (4H, m), 7.30 (1H, d), 1.38 (12H, s).

Provenance & Evidence