반응 #60609

반응 방정식

diisopropylamine

solution 5

7-bromo-5-fluoro-1H-indole-2-carboxylic acid

methoxybenzylamine

PyBOP

→

6

수율 81.0%

7-bromo-5-fluoro-1H-indole-2-carboxylic acid 3-methoxy-benzylamide

수율 81.0%

용매

—

Hexanes

ethyl acetate

반응 조건

후처리

1. 1
   기타To a round bottom flask that has been
2. 2
   기타fire dried
3. 3
   기타flushed with a continuous stream of argon
4. 4
   기타equipped with a stir bean, DMF (4.8 ml)
5. 5
   workup.ADDITIONwas added
6. 6
   추출extracted 3× with saturated sodium bicarbonate, and 3× with 1M HCl in appropriate volumes
7. 7
   기타to remove
8. 8
   기타The ethyl acetate layer was isolated
9. 9
   건조dried over sodium sulfate
10. 10
    기타The ethyl acetate was removed
11. 11
    기타a rotary evaporator
12. 12
    기타to yield a brownish film on the sides of the flask
13. 13
    온도refluxed
14. 14
    기타A solid then formed on the sides of the flask
15. 15
    기타the hexanes were removed via rotary evaporator

실험 절차

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) δ 11.537 (bs, 1H), δ 9.092 (t, J=5.6 Hz, 1H), δ 7.49 (dd, J=9.4 Hz, J=2.4 Hz 1H), δ (dd, J=8.8 Hz, J=2 Hz 1H), δ 7.268-7.228 (m, 2H), δ 6.91 (d, J=6.8 Hz, 2H), δ 6.82 (d, J=8.2 Hz, 1H), δ 4.48 (d, J=6 Hz, 2H), δ 3.729 (s, 3H).

출처