1,2-Dichloroethane → Benzoic Acid

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).

1. washwashed with water and brine
2. concentrationconcentrated
3. additionThe residue was treated with 40 ml of MeOH and 20 ml of 1H NaOH
4. stirringThe reaction mixture was stirred at room temperature for 4 hr
5. concentrationconcentrated via a rotor-evaporator
6. customto remove the methanol
7. filtrationThe solid was filtered
8. washwashed with water
9. custompurified by either recrystalization with CH2Cl2/Hexane or flash column

ORD record

ord-54b90c2167764914b125991d4f9bba26

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06596772B1