Sodium Hydroxide → 1-Cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

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Reaction Conditions

Reaction Steps

To a stirred solution of 1-cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester (150.0 mg, 0.33 mmol) in anhydrous THF (3.5 mL) and anhydrous methanol (1.0 mL) under N2 was added freshly prepared 1N aqueous sodium hydroxide (0.66 ml, 2.0 eq). The reaction mixture was stirred at 65° C. for 1 h. The resultant reaction mixture was evaporated in vacuo and azeotroped with toluene (3×5 ml) to give a yellow solid. The yellow solid was redissolved in water (5 mL), and concentrated. Acetic acid (2 drops) was added. A yellow solid precipitated out, and the solid was filtered, rinsed well with water, and dried on high-vacuum pump to give 243.6 mg (77.4%) of the product. 1H-NMR (500 MHz, DMSO-d6) δ ppm 8.54 (s, 1H), 8.32 (d, J=6.0 Hz, 1H), 7.95 (br s, 1H), 7.65-7.52 (m, 2H), 7.33 (d, J=8.4 Hz, 1H), 6.67 (t, J=9.6 Hz, 1H), 3.53-3.28 (m, 1H), 1.20-1.07 (m, 2H), 0.85 (m, 2H); LC-MS (method C): [M+H]+=438.0, RT=0.67 min.

Provenance & Evidence