Methyl iodide → Methyl 2-(quinolin-6-YL)propanoate

Temperature

-78 °C

THF (5 ml) was taken in a RBF, diisopropyl amine (0.19 ml, 1.29 mmol) was added and cooled to −78° C. under nitrogen atmosphere. Then n-BuLi (0.8 ml, 1.29 mmol) was added and stirred at same temperature for 30 mins. At this stage methyl 2-(quinolin-6-yl)acetate (0.2 g, 0.99 mmol) was added and stirred at −78° C. for 30 mins. Then methyl iodide (0.17 g, 1.2 mmol) was added and stirred at −78° C. for 30 mins and then slowly brought to rt. At rt the reaction mixture was allowed to stir overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer dried on anhydrous Na2SO4 and EtOAc removed using a rotary evaporator to obtain the crude product, which was purified by column chromatography on 60-120 mesh silica gel and EA and Petether (25:75) as eluent. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.89-8.86 (m, 1H), 8.13 (d, J 7.8, 1H), 8.07 (d, J 8.7, 1H), 7.76-7.64 (m, 2H), 7.42-7.37 (m, 1H), 3.92 (q, J 7.2, 1H), 3.68 (s, 3H), 1.60 (d, J 7.2, 3H).

1. additionwas added
2. stirringstirred at −78° C. for 30 mins
3. stirringstirred at −78° C. for 30 mins
4. customslowly brought to rt
5. customAt rt
6. stirringto stir overnight
7. customThe reaction mixture was quenched with water
8. extractionextracted with EtOAc
9. dry with materialThe organic layer dried on anhydrous Na2SO4 and EtOAc
10. customremoved
11. customa rotary evaporator

ORD record

ord-19659580e97b446fa5a46de5afbb7f7e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993612B2