Potassium Carbonate → 6-(4-Cyanophenoxy)-2-(4-trifluoromethoxyphenoxy)nicotinic acid ethyl ester

Temperature

80 °C

Potassium carbonate (60 mg, 0.43 mmol) was added to a stirred and cooled (0° C.) solution of 2-chloro-6-(4-cyano phenoxy)nicotinic acid ethyl ester 0.13 g (0.43 mmol) in 10 ml DMF and stirred for 10 min at the same temperature. This was followed by the addition of 76.5 mg (0.43 mmol) of 4-trifluoromethoxy phenol, dissolved in 2 ml of DMF, over a period of 10 min. After the addition was completed, the contents were allowed to stir at RT. This was followed by heating for 3 h at 80° C. The reaction mixture was concentrated under reduced pressure, poured into ice-cold water and dissolved in 50 ml of ethyl acetate. Organic layer was then washed with brine solution followed by water and the crude product was purified by column chromatography using hexane:ethyl acetate (8:2) to afford 0.18 g of the required product. Percentage purity: LCMS−ve mode): 20.12%.

1. stirringstirred for 10 min at the same temperature
2. additionAfter the addition
3. stirringto stir at RT
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additionpoured into ice-cold water
6. dissolutiondissolved in 50 ml of ethyl acetate
7. washOrganic layer was then washed with brine solution
8. customthe crude product was purified by column chromatography

ORD record

ord-7a43184c2d8e43cc9265eef113be0a6c

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722930B2