Diisopropylamine → 7-bromo-5-fluoro-1H-indole-2-carboxylic Acid 3-methoxy-benzylamide

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask that has been fire dried, flushed with a continuous stream of argon, and equipped with a stir bean, DMF (4.8 ml) was added. To this stirring solution 5 (600 mg, 2.33 mmol), was combined with methoxybenzylamine (328 L, 2.56 mmol), and PyBOP (1.33 g, 2.56 mmol). This solution was then cooled to a temperature of 0 degrees C. After 2 minutes diisopropylamine (1.7 ml, 9.67 mmol) was added and the entire solution was allowed to stir at room temperature overnight. The reaction was then diluted with roughly 60 ml of ethyl acetate and extracted 3× with saturated sodium bicarbonate, and 3× with 1M HCl in appropriate volumes to remove any unreacted starting materials. The ethyl acetate layer was isolated and dried over sodium sulfate. The ethyl acetate was removed using a rotary evaporator to yield a brownish film on the sides of the flask. Hexanes were added to the flask and refluxed. A solid then formed on the sides of the flask, and the hexanes were removed via rotary evaporator to give 709.0 mg of 6 (81% yield). 1H NMR (400 MHz, DMSO-d6) δ11.537 (bs, 1H), δ9.092 (t, J=5.6 Hz, 1H), δ7.49 (dd, J=9.4 Hz, J=2.4 Hz 1H), δ (dd, J=8.8 Hz, J=2 Hz 1H), δ7.268–7.228 (m, 2H), δ6.91 (d, J=6.8 Hz, 2H), δ6.82 (d, J=8.2 Hz, 1H), δ4.48 (d, J=6 Hz, 2H), δ3.729 (s, 3H).

Provenance & Evidence