1,2-Dichloroethane → Benzoic Acid

Participants

Reaction Steps

To 1-Methyl-5-Trifluoromethansulfonylamino-1H-Indole-2-Carboxylic Acid (0.51 g, 1.6 mmol) in 8 ml of DMF was added HOBt (240 mg, 1.8 mmol), EDC (370 mg, 1.9 mmol), TEA (0.445, 3.2 mmol), and 3-aminobenzoic acid ethyl ester (265 mg, 1.6 mmol). The reaction mixture was stirred at room temperature for a day. The reaction was diluted with 200 ml of methylene dichloride and washed with water and brine, then concentrated. The residue was treated with 40 ml of MeOH and 20 ml of 1H NaOH. The reaction mixture was stirred at room temperature for 4 hr and then concentrated via a rotor-evaporator to remove the methanol. The aqueous solution was adjusted pH to 4 with 6N HCl. The solid was filtered, washed with water, and purified by either recrystalization with CH2Cl2/Hexane or flash column using 30% EtOAc/Hexane with 1% AcOH to give 0.19 g of 3-[1-Methyl-5-trifluoromethansulfonylamino-1H-indole-2-carbonyl)-amino]-benzoic acid as a beige solid. 1H-NMR (400 MHz, DMSO-d6) δ 12.75 (s, 1H, COOH), 11.68 (s, 1H, SNH), 10.65 (s, 1H, NHCO), 7.93 (m, 4H, ArH), 7.64 (m, 2H, H-7 & H-4), 7.38 (s, 1H, H-3), 7.20 (dd, J=1.6, 9 Hz, H-6), 4.01 (s, 3H, CH3), MS, m/z, 440 (M−H).

Provenance & Evidence